Benzeneacetic acid, α-broMo-2-Methoxy-, Methyl ester

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: 146.6 ml (1.57 moles) of phosphorus tribromide are added dropwise to 109.7 g (0.562 mole) of methyl 2-methoxymandelate, while cooling well. After 3 hours stirring at room temperature, the mixture is poured into 3N NaCl solution, and extracted with methylene chloride. After washing the organic phase with water, it is dried with Na2SO4 and is concentrated. 140.7 g of the title compound are obtained as a yellowish oil which is used further without purification. while cooling well extracted with methylene chloride After washing the organic phase with water, it is dried with Na2SO4 is concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.61 g (12.7 mmol) of ethyl 2-oxo-2,3-dihydrobenzimidazole-1-carboxylate (IV) were dissolved in dry DMF (40 ml) in a heat-dried flask under a nitrogen atmosphere. 532 mg (13.3 mmol) of sodium hydride (60% suspension in mineral oil) were added while stirring at 0° C., and the reaction solution was then stirred at room temperature for 30 min. After renewed cooling in an ice bath, 3.54 g (13.7 mmol) of methyl bromo-(2-methoxyphenyl)acetate were added and the mixture was stirred while cooling in ice for 1 h and then at room temperature for 2 h. The reaction solution was diluted with ethyl acetate, mixed with 10% aqueous ammonium chloride solution and then extracted with ethyl acetate (3×). The combined organic phases were washed with water and saturated NaCl solution, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (mobile phase 50% ethyl acetate in heptane). Yield: 3.21 g (66%) of colorless oil the reaction solution was then stirred at room temperature for 30 min After renewed cooling in an ice bath the mixture was stirred while cooling in ice for 1 h extracted with ethyl acetate (3×) The combined organic phases were washed with water and saturated NaCl solution dried over magnesium sulfate concentrated in vacuo The residue was purified by chromatography on silica gel (mobile phase 50% ethyl acetate in heptane)

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

Procedure: A mixture of 14.6 g (81.2 mmol) of methyl (2-methoxyphenyl)acetate, 15.2 g (85.3 mmol) of N-bromosuccinimide and a catalytic amount of AIBN in tetrachloromethane (180 ml) was heated under reflux with stirring for 2 h. The cooled reaction solution was filtered, and the solvent was removed in vacuo. Yield: 21.6 g (100%) of yellow oil under reflux The cooled reaction solution was filtered the solvent was removed in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.61 g (12.7 mmol) of ethyl 2-oxo-2,3-dihydrobenzimidazole-1-carboxylate (IV) were dissolved in dry DMF (40 ml) in a heat-dried flask under a nitrogen atmosphere. 532 mg (13.3 mmol) of sodium hydride (60% suspension in mineral oil) were added while stirring at 0° C., and the reaction solution was then stirred at room temperature for 30 min. After renewed cooling in an ice bath, 3.54 g (13.7 mmol) of methyl bromo-(2-methoxyphenyl)acetate were added and the mixture was stirred while cooling in ice for 1 h and then at room temperature for 2 h. The reaction solution was diluted with ethyl acetate, mixed with 10% aqueous ammonium chloride solution and then extracted with ethyl acetate (3×). The combined organic phases were washed with water and saturated NaCl solution, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (mobile phase 50% ethyl acetate in heptane). Yield: 3.21 g (66%) of colorless oil the reaction solution was then stirred at room temperature for 30 min After renewed cooling in an ice bath the mixture was stirred while cooling in ice for 1 h extracted with ethyl acetate (3×) The combined organic phases were washed with water and saturated NaCl solution dried over magnesium sulfate concentrated in vacuo The residue was purified by chromatography on silica gel (mobile phase 50% ethyl acetate in heptane)

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

Procedure: A mixture of 14.6 g (81.2 mmol) of methyl (2-methoxyphenyl)acetate, 15.2 g (85.3 mmol) of N-bromosuccinimide and a catalytic amount of AIBN in tetrachloromethane (180 ml) was heated under reflux with stirring for 2 h. The cooled reaction solution was filtered, and the solvent was removed in vacuo. Yield: 21.6 g (100%) of yellow oil under reflux The cooled reaction solution was filtered the solvent was removed in vacuo