4-Chloro-2,6-dimethybenzaldehyde

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: Dissolve 4-chloro-2,6-dimethyl benzaldehyde (5.0 g, 168.64 g/mol) in 100 mL dry MeOH. Cool to 0° C. while stirring under N2. Portionwise add powdered NaBH4 (0.76 g, 37.85 g/mol) over 5 min. Stir at 0° C. for 2 h, monitoring by TLC until aldehyde consumed, then evaporate to a yellow oil. Add H2O (50 mL) and bring to pH 7.0 by addition of saturated NH4Cl. Extract the neutral aqueous layer with CH2Cl2 (3×75 mL) and dry the pooled organic layers over Na2SO4. Filter and concentrate to a yellow oil. Flush through a pad of silica to remove baseline material, then evaporate to a yellow solid (3.0 g) which can be used without further purification. LCMS=171.6 (MH+), 169.6 (M−). Stir at 0° C. for 2 h monitoring by TLC until aldehyde consumed evaporate to a yellow oil Add H2O (50 mL) and bring to pH 7.0 by addition of saturated NH4Cl Extract the neutral aqueous layer with CH2Cl2 (3×75 mL) dry the pooled organic layers over Na2SO4 Filter concentrate to a yellow oil Flush through a pad of silica to remove baseline material evaporate to a yellow solid (3.0 g) which can be used without further purification

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

実験手順: Dissolve 4-chloro-2,6-dimethyl benzaldehyde (5.0 g, 168.64 g/mol) in 100 mL dry MeOH. Cool to 0° C. while stirring under N2. Portionwise add powdered NaBH4 (0.76 g, 37.85 g/mol) over 5 min. Stir at 0° C. for 2 h, monitoring by TLC until aldehyde consumed, then evaporate to a yellow oil. Add H2O (50 mL) and bring to pH 7.0 by addition of saturated NH4Cl. Extract the neutral aqueous layer with CH2Cl2 (3×75 mL) and dry the pooled organic layers over Na2SO4. Filter and concentrate to a yellow oil. Flush through a pad of silica to remove baseline material, then evaporate to a yellow solid (3.0 g) which can be used without further purification. LCMS=171.6 (MH+), 169.6 (M−). Stir at 0° C. for 2 h monitoring by TLC until aldehyde consumed evaporate to a yellow oil Add H2O (50 mL) and bring to pH 7.0 by addition of saturated NH4Cl Extract the neutral aqueous layer with CH2Cl2 (3×75 mL) dry the pooled organic layers over Na2SO4 Filter concentrate to a yellow oil Flush through a pad of silica to remove baseline material evaporate to a yellow solid (3.0 g) which can be used without further purification

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

実験手順: Dissolve 4-bromo-3,5-dimethyl chlorobenzene (6.5 g) in 50 mL anhydrous THF and cool to −78° C. (dry ice/acetone) under N2. Dropwise over 5 min add a solution of butyllithium (12.50 mL, 2.5M in hexanes) to the stirring solution of aryl bromide at −78° C. After 2 h, dropwise add anhydrous DMF (5.0 mL) to the orange/red reaction solution and allow to warn to ambient temperature overnight while stirring under N2. Evaporate the yellow solution down to a yellow oil and partition between H2O (100 mL) and CH2Cl2 (100 mL). Extract the aqueous layer once with CH2Cl2, then pool the organic layers and dry over Na2SO4, filter and evaporate down to 5.0 g of yellow oil. Use without further purification. LCMS=169.6 (MH+). to warn to ambient temperature overnight Evaporate the yellow solution down to a yellow oil partition between H2O (100 mL) and CH2Cl2 (100 mL) Extract the aqueous layer once with CH2Cl2 dry over Na2SO4 filter evaporate down to 5.0 g of yellow oil Use without further purification

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

実験手順: Dissolve 4-chloro-2,6-dimethyl benzaldehyde (5.0 g, 168.64 g/mol) in 100 mL dry methanol. Cool to 0° C. while stirring under N2. Portionwise add powdered NaBH4 (0.76g, 37.85 g/mol) over 5 minutes. Stir at 0° C. for 2 hours, monitoring by TLC until aldehyde consumed, then evaporate to a yellow oil. Add H2O (50 mL) and bring to pH. 7.0 by addition of saturated NH4Cl. Extract the neutral aqueous layer with CH2Cl2 (3×75 mL) and dry the pooled organic layers over Na2SO4. Filter and concentrate to a yellow oil. Flush through a pad of silica to remove baseline material, then evaporate to a yellow solid (3.0 g) which can be used without further purification. LCMS=171.6 (MH+), 169.6 (M−) Stir at 0° C. for 2 hours monitoring by TLC until aldehyde consumed evaporate to a yellow oil 7.0 by addition of saturated NH4Cl Extract the neutral aqueous layer with CH2Cl2 (3×75 mL) dry the pooled organic layers over Na2SO4 Filter concentrate to a yellow oil Flush through a pad of silica to remove baseline material evaporate to a yellow solid (3.0 g) which can be used without further purification

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

実験手順: Dissolve 4-chloro-2,6-dimethyl benzaldehyde (5.0 g, 168.64 g/mol) in 100 mL dry methanol. Cool to 0° C. while stirring under N2. Portionwise add powdered NaBH4 (0.76g, 37.85 g/mol) over 5 minutes. Stir at 0° C. for 2 hours, monitoring by TLC until aldehyde consumed, then evaporate to a yellow oil. Add H2O (50 mL) and bring to pH. 7.0 by addition of saturated NH4Cl. Extract the neutral aqueous layer with CH2Cl2 (3×75 mL) and dry the pooled organic layers over Na2SO4. Filter and concentrate to a yellow oil. Flush through a pad of silica to remove baseline material, then evaporate to a yellow solid (3.0 g) which can be used without further purification. LCMS=171.6 (MH+), 169.6 (M−) Stir at 0° C. for 2 hours monitoring by TLC until aldehyde consumed evaporate to a yellow oil 7.0 by addition of saturated NH4Cl Extract the neutral aqueous layer with CH2Cl2 (3×75 mL) dry the pooled organic layers over Na2SO4 Filter concentrate to a yellow oil Flush through a pad of silica to remove baseline material evaporate to a yellow solid (3.0 g) which can be used without further purification

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

実験手順: Dissolve 4-bromo-3,5-dimethyl chlorobenzene (6.5 g) in 50 mL anhydrous THF and cool to −78° C. (dry ice/acetone) under N2. Dropwise over 5 minutes add a solution of butyllithium (12.50 mL, 2.5M in hexanes) to the stirring solution of aryl bromide at −78° C. After 2 hours, dropwise add anhydrous DMF (5.0 mL) to the orange/red reaction solution and allow to warn to ambient temperature overnight while stirring under N2. Evaporate the yellow solution down to a yellow oil and partition between H2O (100 mL) and CH2Cl2 (100 mL). Extract the aqueous layer once with CH2Cl2, then pool the organic layers and dry over Na2SO4, filter and evaporate down to 5.0 g of yellow oil. Use without further purification. LCMS=169.6 (MH+) to warn to ambient temperature overnight Evaporate the yellow solution down to a yellow oil partition between H2O (100 mL) and CH2Cl2 (100 mL) Extract the aqueous layer once with CH2Cl2 dry over Na2SO4 filter evaporate down to 5.0 g of yellow oil Use without further purification

反応条件: temp:0.00; pressure:0.00; stir:

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: Dissolve 4-bromo-3,5-dimethyl chlorobenzene (6.5 g) in 50 mL anhydrous THF and cool to −78° C. (dry ice/acetone) under N2. Dropwise over 5 min add a solution of butyllithium (12.50 mL, 2.5M in hexanes) to the stirring solution of aryl bromide at −78° C. After 2 h, dropwise add anhydrous DMF (5.0 mL) to the orange/red reaction solution and allow to warn to ambient temperature overnight while stirring under N2. Evaporate the yellow solution down to a yellow oil and partition between H2O (100 mL) and CH2Cl2 (100 mL). Extract the aqueous layer once with CH2Cl2, then pool the organic layers and dry over Na2SO4, filter and evaporate down to 5.0 g of yellow oil. Use without further purification. LCMS=169.6 (MH+). to warn to ambient temperature overnight Evaporate the yellow solution down to a yellow oil partition between H2O (100 mL) and CH2Cl2 (100 mL) Extract the aqueous layer once with CH2Cl2 dry over Na2SO4 filter evaporate down to 5.0 g of yellow oil Use without further purification

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

実験手順: Dissolve 4-chloro-2,6-dimethyl benzaldehyde (5.0 g, 168.64 g/mol) in 100 mL dry MeOH. Cool to 0° C. while stirring under N2. Portionwise add powdered NaBH4 (0.76 g, 37.85 g/mol) over 5 min. Stir at 0° C. for 2 h, monitoring by TLC until aldehyde consumed, then evaporate to a yellow oil. Add H2O (50 mL) and bring to pH 7.0 by addition of saturated NH4Cl. Extract the neutral aqueous layer with CH2Cl2 (3×75 mL) and dry the pooled organic layers over Na2SO4. Filter and concentrate to a yellow oil. Flush through a pad of silica to remove baseline material, then evaporate to a yellow solid (3.0 g) which can be used without further purification. LCMS=171.6 (MH+), 169.6 (M−). Stir at 0° C. for 2 h monitoring by TLC until aldehyde consumed evaporate to a yellow oil Add H2O (50 mL) and bring to pH 7.0 by addition of saturated NH4Cl Extract the neutral aqueous layer with CH2Cl2 (3×75 mL) dry the pooled organic layers over Na2SO4 Filter concentrate to a yellow oil Flush through a pad of silica to remove baseline material evaporate to a yellow solid (3.0 g) which can be used without further purification