2-(2,3,5-trichlorophenyl)acetonitrile

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 6.9 grams (0.031 mole) of 2,3,5-trichlorophenylacetonitrile and 65 mL of water was stirred, and 65 mL of concentrated sulfuric acid was cautiously added. Upon completion of addition, the reaction mixture was heated to reflux, where it was stirred for about 2 hours. After this time the reaction mixture was cooled in an ice-bath and filtered. The collected solid was washed with water and then dissolved in ethyl acetate. The organic layer was washed with two portions of water and then with one portion of an aqueous solution saturated with sodium chloride. The organic layer was then dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 6.3 grams of 2,3,5-trichlorophenylacetic acid, mp 125°-133° C. The NMR spectrum was consistent with the proposed structure. Upon completion of addition the reaction mixture was heated to reflux where it was stirred for about 2 hours After this time the reaction mixture was cooled in an ice-bath filtered The collected solid was washed with water dissolved in ethyl acetate The organic layer was washed with two portions of water The organic layer was then dried with sodium sulfate filtered The filtrate was concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 6.9 grams (0.031 mole) of 2,3,5-trichlorophenylacetonitrile and 65 mL of water was stirred, and 65 mL of concentrated sulfuric acid was cautiously added. Upon completion of addition, the reaction mixture was heated to reflux, where it was stirred for about 2 hours. After this time the reaction mixture was cooled in an ice-bath and filtered. The collected solid was washed with water and then dissolved in ethyl acetate. The organic layer was washed with two portions of water and then with one portion of an aqueous solution saturated with sodium chloride. The organic layer was then dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 6.3 grams of 2,3,5-trichlorophenylacetic acid, mp 125°-133° C. The NMR spectrum was consistent with the proposed structure. Upon completion of addition the reaction mixture was heated to reflux where it was stirred for about 2 hours After this time the reaction mixture was cooled in an ice-bath filtered The collected solid was washed with water dissolved in ethyl acetate The organic layer was washed with two portions of water The organic layer was then dried with sodium sulfate filtered The filtrate was concentrated under reduced pressure

反応条件: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 19.2 grams (0.070 mole) of 2,3,5-trichlorophenylmethyl bromide in 50 mL of methanol was stirred, and a solution of 4.1 grams (0.084 mole) of sodium cyanide in 10 mL of water was added dropwise during a 10 minute period. The addition caused an exothermic reaction which raised the reaction mixture temperature to about 35° C. Upon completion of addition, the reaction mixture was warmed to reflux, where it was stirred for 4.5 hours. The reaction mixture was allowed to cool to ambient temperature, where it was stirred for about 60 hours. After this time the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with two portions of water, two 25 mL portions of aqueous 10% hydrochloric acid, and then with three portions of water. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 10.8 grams of 2,3,5-trichlorophenylacetonitrile. The infrared spectrum was consistent with the proposed structure. The addition an exothermic reaction which Upon completion of addition the reaction mixture was warmed to reflux to cool to ambient temperature where it was stirred for about 60 hours the mixture was extracted with ethyl acetate The extract was washed with two portions of water, two 25 mL portions of aqueous 10% hydrochloric acid The organic layer was dried with sodium sulfate filtered The filtrate was concentrated under reduced pressure

反応条件: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 19.2 grams (0.070 mole) of 2,3,5-trichlorophenylmethyl bromide in 50 mL of methanol was stirred, and a solution of 4.1 grams (0.084 mole) of sodium cyanide in 10 mL of water was added dropwise during a 10 minute period. The addition caused an exothermic reaction which raised the reaction mixture temperature to about 35° C. Upon completion of addition, the reaction mixture was warmed to reflux, where it was stirred for 4.5 hours. The reaction mixture was allowed to cool to ambient temperature, where it was stirred for about 60 hours. After this time the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with two portions of water, two 25 mL portions of aqueous 10% hydrochloric acid, and then with three portions of water. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 10.8 grams of 2,3,5-trichlorophenylacetonitrile. The infrared spectrum was consistent with the proposed structure. The addition an exothermic reaction which Upon completion of addition the reaction mixture was warmed to reflux to cool to ambient temperature where it was stirred for about 60 hours the mixture was extracted with ethyl acetate The extract was washed with two portions of water, two 25 mL portions of aqueous 10% hydrochloric acid The organic layer was dried with sodium sulfate filtered The filtrate was concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of NaOEt (from 0.68 g of sodium) in ethanol (20 ml) was added 2,3,5-trichlorophenylacetonitrile (5 g) and ethyl acetate (4.43 ml). The mixture was heated under reflux, under nitrogen for 2.5 hours. The mixture was left standing at room temperature overnight. The mixture was then concentrated and the residue was dissolved in water. The aqueous phase was washed with ether, acidified with concentrated H2SO4 and extracted with ether. The extracts were bulked, dried (MgSO4) and evaporated, 2.59 g. mp. 134°-135° C. The mixture was heated under reflux, under nitrogen for 2.5 hours The mixture was left The mixture was then concentrated the residue was dissolved in water The aqueous phase was washed with ether extracted with ether dried (MgSO4) evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred refluxing solution of sodium ethoxide (from 1.38 g sodium) in ethanol (25 ml) was added over 5 minutes a mixture of 2,3,5-trichlorophenylacetonitrile (11 g) and ethyl methoxyacetate (8.85 g) in dry DME (25 ml). After 4 hours the mixture was cooled on ice and acidified by dropwise addition of acetic acid (ca. 6 ml), diluted with ice-water (150 ml) and extracted with dichloromethane (2×100 ml). The dichloromethane extract was washed with water, dried over MgSO4 and concentrated giving a yellow solid, which was triturated with a little ether and filtered. 8.6 g Homogeneous by TLC (19:1 CH2Cl2 :MeOH). was added over 5 minutes After 4 hours the mixture was cooled on ice extracted with dichloromethane (2×100 ml) The dichloromethane extract was washed with water dried over MgSO4 concentrated giving a yellow solid, which was triturated with a little ether filtered

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred refluxing solution of sodium ethoxide (from 1.38 g sodium) in ethanol (25 ml) was added over 5 minutes a mixture of 2,3,5-trichlorophenylacetonitrile (11 g) and ethyl methoxyacetate (8.85 g) in dry DME (25 ml). After 4 hours the mixture was cooled on ice and acidified by dropwise addition of acetic acid (ca. 6 ml), diluted with ice-water (10 ml) and extracted with dichloromethane (2×100 ml). The dichloromethane extract was washed with water, dried over MgSO4 and concentrated giving a yellow solid, which was triturated with a little ether and filtered. 8.6 g Homogeneous by TLC (19:1 CH2Cl2 :MeOH). was added over 5 minutes After 4 hours the mixture was cooled on ice extracted with dichloromethane (2×100 ml) The dichloromethane extract was washed with water dried over MgSO4 concentrated giving a yellow solid, which was triturated with a little ether filtered

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of NaOEt (from 0.68 g of sodium) in ethanol (20 ml) was added 2,3,5-trichlorophenylacetonitrile (5 g) and ethyl acetate (4.43 ml). The mixture was heated under reflux, under nitrogen for 2.5 hours. The mixture was left standing at room temperature overnight. The mixture was then concentrated and the residue was dissolved in water. The aqueous phase was washed with ether, acidified with concentrated H2SO4 and extracted with ether. The extracts were bulked, dried (MgSO4) and evaporated, 2.59 g, mp. 134°-135° C. The mixture was heated under reflux, under nitrogen for 2.5 hours The mixture was left The mixture was then concentrated the residue was dissolved in water The aqueous phase was washed with ether extracted with ether dried (MgSO4) evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred refluxing solution of sodium ethoxide (from 1.38 g sodium) in ethanol (25 ml) was added over 5 minutes a mixture of 2,3,5-trichlorophenylacetonitrile (11 g) and ethyl methoxyacetate (8.85 g) in dry DME (25 ml). After 4 hours the mixture was cooled on ice and acidified by dropwise addition of acetic acid (ca. 6 ml), diluted with ice-water (150 ml) and extracted with dichloromethane (2×100 ml). The dichloromethane extract was washed with water, dried over MgSO4 and concentrated giving a yellow solid, which was triturated with a little ether and filtered. 8.6 g Homogeneous by TLC (19:1 CH2Cl2 :MeOH). was added over 5 minutes After 4 hours the mixture was cooled on ice extracted with dichloromethane (2×100 ml) The dichloromethane extract was washed with water dried over MgSO4 concentrated giving a yellow solid, which was triturated with a little ether filtered

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of NaOEt (from 0.68 g of sodium) in ethanol (20 ml) was added 2,3,5-trichlorophenylacetonitrile (5 g) and ethyl acetate (4.43 ml). The mixture was heated under reflux, under nitrogen for 2.5 hours. The mixture was left standing at room temperature overnight. The mixture was then concentrated and the residue was dissolved in water. The aqueous phase was washed with ether, acidified with concentrated H2SO4 and extracted with ether. The extracts were bulked, dried (MgSO4) and evaporated, 2.59 g, mp. 134°-135° C. The mixture was heated under reflux, under nitrogen for 2.5 hours The mixture was left The mixture was then concentrated the residue was dissolved in water The aqueous phase was washed with ether extracted with ether dried (MgSO4) evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of NaOEt (from 0.68 g of sodium) in ethanol (20 ml) was added 2,3,5-trichlorophenylacetonitrile (5 g) and ethyl acetate (4.43 ml). The mixture was heated under reflux, under nitrogen for 2.5 hours. The mixture was left standing at room temperature overnight. The mixture was then concentrated and the residue was dissolved in water. The aqueous phase was washed with ether, acidified with concentrated H2SO4 and extracted with ether. The extracts were bulked, dried (MgSO4) and evaporated, 2.59 g, mp. 134°-135° C. The mixture was heated under reflux, under nitrogen for 2.5 hours The mixture was left The mixture was then concentrated the residue was dissolved in water The aqueous phase was washed with ether extracted with ether dried (MgSO4) evaporated