2-BROMO-6-CHLOROBENZYL BROMIDE

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: 1 cis/trans 2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropane carboxylic acid (2.3 g), 2-bromo-6-chlorobenzylbromide (2.85 g) and potassium carbonate (1.6 g) were stirred together in acetone (30 ml) under reflux for 6 hours. The reaction mixture was cooled, diluted with water, and extracted three times with 50 ml portions of diethyl ether. The combined ether extracts were washed with water and with aqueous sodium bicarbonate solution (three times), dried over magnesium sulphate and evaporated to give the orange title product (4. g, 98%) m.p. 61°-67° C. under reflux for 6 hours The reaction mixture was cooled extracted three times with 50 ml portions of diethyl ether The combined ether extracts were washed with water and with aqueous sodium bicarbonate solution (three times) dried over magnesium sulphate evaporated

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

実験手順: 2-bromo-6-chlorotoluene (20.55 g) and N-bromosuccinimide (19.6 g) were stirred together in carbon tetrachloride (100 ml) under reflux for 22 hours exposure to radiation from an infrared lamp. The resulting solution was cooled in ice, filtered and evaporated to yield the title product which was dissolved in petroleum ether (60-80). Part was recrystallised therefrom as pink needles (8.5 g) and part was recovered by evaporation as a dark orange solid (17.7 g) (total yield 26.2 g. 92%). under reflux for 22 hours exposure to radiation from an infrared lamp The resulting solution was cooled in ice filtered evaporated

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

実験手順: 1 cis/trans 2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropane carboxylic acid (2.3 g), 2-bromo-6-chlorobenzylbromide (2.85 g) and potassium carbonate (1.6 g) were stirred together in acetone (30 ml) under reflux for 6 hours. The reaction mixture was cooled, diluted with water, and extracted three times with 50 ml portions of diethyl ether. The combined ether extracts were washed with water and with aqueous sodium bicarbonate solution (three times), dried over magnesium sulphate and evaporated to give the orange title product (4. g, 98%) m.p. 61°-67° C. under reflux for 6 hours The reaction mixture was cooled extracted three times with 50 ml portions of diethyl ether The combined ether extracts were washed with water and with aqueous sodium bicarbonate solution (three times) dried over magnesium sulphate evaporated

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

実験手順: 2-bromo-6-chlorotoluene (20.55 g) and N-bromosuccinimide (19.6 g) were stirred together in carbon tetrachloride (100 ml) under reflux for 22 hours exposure to radiation from an infrared lamp. The resulting solution was cooled in ice, filtered and evaporated to yield the title product which was dissolved in petroleum ether (60-80). Part was recrystallised therefrom as pink needles (8.5 g) and part was recovered by evaporation as a dark orange solid (17.7 g) (total yield 26.2 g. 92%). under reflux for 22 hours exposure to radiation from an infrared lamp The resulting solution was cooled in ice filtered evaporated

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 solution of 31.3 g of the crude 6-chloro-alpha,2-dibromotoluene in 100 ml of warm ethanol is treated with a solution of 6.7 g of potassium cyanide in 10 ml of water and the mixture is heated at reflux for 4 hours. The crude product is isolated by pouring the cooled reaction mixture into water and filtering the resulting precipitate. Recrystallization of this solid from aqueous ethanol then gives 12.4 g of 2-bromo-6-chlorophenylacetonitrile, mp 82°-84° C. the mixture is heated at reflux for 4 hours The crude product is isolated by pouring filtering the resulting precipitate Recrystallization of this solid from aqueous ethanol

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Diethyl malonate (8.33 mL, 54.59 mmol) was added dropwise to sodium hydride (60% oil dispersion) (2.28 g, 56.97 mmol) in DMF (55 mL) at 0° C. The mixture was stirred for 5 min at ambient temp, wherafter 1-bromo-2-(bromomethyl)-3-chlorobenzene (13.5 g, 47.5 mmol) dissolved in DMF (15 mL) was added dropwise at 0° C. The mixture was stirred at 0° C. for 20 min and ambient temp overnight. NH4Cl (aq) was added to quench the reaction. Diethyl ether was added followed by water. The phases were separated and the aqueous phase was extracted with diethyl ether. The combined organic phases were washed with brine and dried (MgSO4). The aqueous phase was extracted with dichloromethane. The organic phase was washed with brine. The solvents were evaporated to give 18.2 g (quantitative). 4 g of the crude material was dissolved in dichloromethane and purified by column chromatography eluting with gradients of ethyl acetate in heptanes. Fractions containing product were pooled and the solvents were evaporated to give the title compound. Yield: 3.32 g, 19%. 1H NMR (400 MHz, CDCl3) δ ppm 1.23 (t, 7H) 3.62 (d, 2H) 3.84 (m, 1H) 4.20 (q, 4H) 7.06 (t, 1H) 7.35 (dd, 1H) 7.50 (dd, 1H). MS (ES+) m/z 365 [M+H]+. was added dropwise at 0° C to quench the reaction The phases were separated the aqueous phase was extracted with diethyl ether The combined organic phases were washed with brine dried (MgSO4) The aqueous phase was extracted with dichloromethane The organic phase was washed with brine The solvents were evaporated to give 18.2 g (quantitative) purified by column chromatography eluting with gradients of ethyl acetate in heptanes Fractions containing product the solvents were evaporated

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

実験手順: 1 cis/trans 2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropane carboxylic acid (2.3 g), 2-bromo-6-chlorobenzylbromide (2.85 g) and potassium carbonate (1.6 g) were stirred together in acetone (30 ml) under reflux for 6 hours. The reaction mixture was cooled, diluted with water, and extracted three times with 50 ml portions of diethyl ether. The combined ether extracts were washed with water and with aqueous sodium bicarbonate solution (three times), dried over magnesium sulphate and evaporated to give the orange title product (4. g, 98%) m.p. 61°-67° C. under reflux for 6 hours The reaction mixture was cooled extracted three times with 50 ml portions of diethyl ether The combined ether extracts were washed with water and with aqueous sodium bicarbonate solution (three times) dried over magnesium sulphate evaporated

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

実験手順: 2-bromo-6-chlorotoluene (20.55 g) and N-bromosuccinimide (19.6 g) were stirred together in carbon tetrachloride (100 ml) under reflux for 22 hours exposure to radiation from an infrared lamp. The resulting solution was cooled in ice, filtered and evaporated to yield the title product which was dissolved in petroleum ether (60-80). Part was recrystallised therefrom as pink needles (8.5 g) and part was recovered by evaporation as a dark orange solid (17.7 g) (total yield 26.2 g. 92%). under reflux for 22 hours exposure to radiation from an infrared lamp The resulting solution was cooled in ice filtered evaporated