octyl 2-bromoacetate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 20 g of bromoacetic acid, 22 g of n-decyl alcohol, and 2.5 g of p-toluenesulfonic acid were added to 150 ml of toluene, and the azeotropic dehydration was carried out for 1.5 hours. After cooling the mixture by allowing it to stand, the toluene was removed under reduced pressure and then vacuum distillation was performed, to obtain 41 g of n-octyl bromoacetate (121° C., 10 mmHg). After cooling the mixture the toluene was removed under reduced pressure vacuum distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: There were added to 150 ml of toluene, 20 g of bromoacetic acid, 20 g of n-octyl alcohol and 2.5 g of p-toluenesulfonic acid, and azeotropical dehydration was carried out for 1.5 hours. After cooling, toluene was distilled off at reduced pressure, and 41 g of n-octyl bromoacetate were obtained by vacuum distillation (110° C., 11 mm Hg). After cooling toluene was distilled off at reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: There were added to 150 ml of toluene, 20 g of bromoacetic acid, 20 g of n-octyl alcohol and 2.5 g of p-toluenesulfonic acid, and azeotropical dehydration was carried out for 1.5 hours. After cooling, toluene was distilled off at reduced pressure, and 41 g of n-octyl bromoacetate were obtained by vacuum distillation (110° C., 11 mm Hg). After cooling toluene was distilled off at reduced pressure

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of lithium diisopropylamide (prepared from 4.8 g, (47.8 mmol) of diisopropylamine and 19.1 ml, (2.5M, 47.8 mmol) of n-BuLi) in 50 ml of THF was added isobutyric acid (2.2 ml, 23.9 mmol) at 0° C. and the mixture was allowed to warm to 45° C. with stirring. To the mixture cooled to -78° C., was added 4.3 g (23.9 mmol) of HMPA followed by a solution of 1-octyl bromoacetate (6 g, 23.9 mmol) in 50 ml of THF under argon at -78° C. The mixture was quenched with 1N HCl, warmed to room temperature, and extracted with ether (3×50ml). The organic layer was dried over magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (10% methanol/ethyl acetate) to afford 0.8 g of 3-(1-octyloxycarbonyl)-2,2-dimethylbutyric acid. To the mixture cooled to -78° C. The mixture was quenched with 1N HCl warmed to room temperature extracted with ether (3×50ml) The organic layer was dried over magnesium sulfate concentrated in vacuo purified by flash chromatography (10% methanol/ethyl acetate)

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of lithium diisopropylamide (prepared from 4.8 g, (47.8 mmol) of diisopropylamine and 19.1 ml, (2.5M, 47.8 mmol) of n-BuLi) in 50 ml of THF was added isobutyric acid (2.2 ml, 23.9 mmol) at 0° C. and the mixture was allowed to warm to 45° C. with stirring. To the mixture cooled to -78° C., was added 4.3 g (23.9 mmol) of HMPA followed by a solution of 1-octyl bromoacetate (6 g, 23.9 mmol) in 50 ml of THF under argon at -78° C. The mixture was quenched with 1N HCl, warmed to room temperature, and extracted with ether (3×50ml). The organic layer was dried over magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (10% methanol/ethyl acetate) to afford 0.8 g of 3-(1-octyloxycarbonyl)-2,2-dimethylbutyric acid. To the mixture cooled to -78° C. The mixture was quenched with 1N HCl warmed to room temperature extracted with ether (3×50ml) The organic layer was dried over magnesium sulfate concentrated in vacuo purified by flash chromatography (10% methanol/ethyl acetate)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Bromoacetyl bromide (20 g, 99.1 mmol) was added to a solution of 1-octanol (12.9 g, 99.1 mmol) and 10 ml of pyridine in 100 ml of methylene chloride at 0° C. After 10 minutes, the mixture was quenched with 100 ml of ice/water, and the aqueous layer was extracted with methylene chloride, and the combined organic layer was washed with 1N HCl (3×100ml) and brine. The organic layer was dried over magnesium sulfate, concentrated in vacuo, and the product was distilled under high vacuum to afford 6 g of 1-octyl bromoacetate as an oil, b.p. 93° C. the mixture was quenched with 100 ml of ice/water the aqueous layer was extracted with methylene chloride the combined organic layer was washed with 1N HCl (3×100ml) and brine The organic layer was dried over magnesium sulfate concentrated in vacuo the product was distilled under high vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 20 g of bromoacetic acid, 22 g of n-decyl alcohol, and 2.5 g of p-toluenesulfonic acid were added to 150 ml of toluene, and the azeotropic dehydration was carried out for 1.5 hours. After cooling the mixture by allowing it to stand, the toluene was removed under reduced pressure and then vacuum distillation was performed, to obtain 41 g of n-octyl bromoacetate (121° C., 10 mmHg). After cooling the mixture the toluene was removed under reduced pressure vacuum distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 20 g of bromoacetic acid, 22 g of n-decyl alcohol, and 2.5 g of p-toluenesulfonic acid were added to 150 ml of toluene, and the azeotropic dehydration was carried out for 1.5 hours. After cooling the mixture by allowing it to stand, the toluene was removed under reduced pressure and then vacuum distillation was performed, to obtain 41 g of n-octyl bromoacetate (121° C., 10 mmHg). After cooling the mixture the toluene was removed under reduced pressure vacuum distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: There were added to 150 ml of toluene, 20 g of bromoacetic acid, 20 g of n-octyl alcohol and 2.5 g of p-toluenesulfonic acid, and azeotropical dehydration was carried out for 1.5 hours. After cooling, toluene was distilled off at reduced pressure, and 41 g of n-octyl bromoacetate were obtained by vacuum distillation (110° C., 11 mm Hg). After cooling toluene was distilled off at reduced pressure

Conditions: temp:0.00; pressure:0.00; stir: