methyl 2-(2-chlorophenyl)acetate

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

Procedure: To 2-chlorophenylacetic acid (1.04 g, 6 mmol) in MeOH (25 mL) was added sulfuric acid (6 drops) and the solution was refluxed for 16 hours. After concentration, the residue was taken up in ethyl acetate and washed with sat'd aq. NaHCO3, H2O and brine. The organic layer was dried over Na2SO4 and concentrated to give methyl (2-chlorophenyl)acetate 6a (1.08 g, 97.5% ) as a yellowish oil. GCMS (EI) m/z 184, 186 (M+). the solution was refluxed for 16 hours After concentration washed with sat'd aq. NaHCO3, H2O and brine The organic layer was dried over Na2SO4 concentrated

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

Procedure: A solution of 2-chlorophenylacetic acid (10.0 g) in methanol (100 ml) containing 1 drop of concentrated sulphuric acid was heated at reflux for 2 hours. The reaction mixture was evaporated to half volume and partitioned between ethyl acetate (100 ml) and water (100 ml). The organic phase was dried over magnesium sulphate and evaporated to give the title compound (10.0 g) as a colourless oil. was heated at reflux for 2 hours The reaction mixture was evaporated to half volume partitioned between ethyl acetate (100 ml) and water (100 ml) The organic phase was dried over magnesium sulphate evaporated

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

Procedure: To 2-chlorophenylacetic acid (1.04 g, 6 mmol) in MeOH (25 mL) was added sulfuric acid (6 drops) and the solution was refluxed for 16 hours. After concentration, the residue was taken up in ethyl acetate and washed with sat'd aq. NaHCO3, H2O and brine. The organic layer was dried over Na2SO4 and concentrated to give methyl (2-chlorophenyl)acetate 6a (1.08 g, 97.5% ) as a yellowish oil. GCMS (EI) m/z 184, 186 (M+). the solution was refluxed for 16 hours After concentration washed with sat'd aq. NaHCO3, H2O and brine The organic layer was dried over Na2SO4 concentrated

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

Procedure: A stirred mixture of 36.9 g of methyl o-chlorophenylacetate, 36.0 g of N-bromosuccinimide, and 2 drops of 48% hydrobromic acid in 500 ml of carbon tetrachloride is refluxed for 20 hours and then filtered through magnesium silicate. Evaporation under reduced pressure gives methyl α-bromo-o-chlorophenylacetate as a straw-colored liquid. is refluxed for 20 hours filtered through magnesium silicate Evaporation under reduced pressure

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

Procedure: A stirred mixture of 36.9 g of methyl o-chlorophenylacetate, 36.0 g of N-bromosuccinimide, and 2 drops of 48% hydrobromic acid in 500 ml of carbon tetrachloride is refluxed for 20 hours and then filtered through magnesium silicate. Evaporation under reduced pressure gives methyl α-bromo-o-chlorophenylacetate as a straw-colored liquid. is refluxed for 20 hours filtered through magnesium silicate Evaporation under reduced pressure

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

Procedure: To 2-chlorophenylacetic acid (1.04 g, 6 mmol) in MeOH (25 mL) was added sulfuric acid (6 drops) and the solution was refluxed for 16 hours. After concentration, the residue was taken up in ethyl acetate and washed with sat'd aq. NaHCO3, H2O and brine. The organic layer was dried over Na2SO4 and concentrated to give methyl (2-chlorophenyl)acetate 6a (1.08 g, 97.5%) as a yellowish oil. GCMS (EI) m/z 184, 186 (M+). the solution was refluxed for 16 hours After concentration washed with sat'd aq. NaHCO3, H2O and brine The organic layer was dried over Na2SO4 concentrated

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

Procedure: A stirred mixture of 36.9 g of methyl o-chlorophenylacetate, 36.0 g of N-bromosuccinimide, and 2 drops of 48% hydrobromic acid in 500 ml of carbon tetrachloride is refluxed for 20 hours and then filtered through magnesium silicate. Evaporation under reduced pressure gives methyl α-bromo-o-chlorophenylacetate as a straw-colored liquid. is refluxed for 20 hours filtered through magnesium silicate Evaporation under reduced pressure

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

Procedure: A stirred mixture of 36.9 g of methyl o-chlorophenylacetate, 36.0 g of N-bromosuccinimide, and 2 drops of 48% hydrobromic acid in 500 ml of carbon tetrachloride is refluxed for 20 hours and then filtered through magnesium silicate. Evaporation under reduced pressure gives methyl α-bromo-o-chlorophenylacetate as a straw-colored liquid. is refluxed for 20 hours filtered through magnesium silicate Evaporation under reduced pressure

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

Procedure: To 2-chlorophenylacetic acid (1.04 g, 6 mmol) in MeOH (25 mL) was added sulfuric acid (6 drops) and the solution was refluxed for 16 hours. After concentration, the residue was taken up in ethyl acetate and washed with sat'd aq. NaHCO3, H2O and brine. The organic layer was dried over Na2SO4 and concentrated to give methyl (2-chlorophenyl)acetate 6a (1.08 g, 97.5%) as a yellowish oil. GCMS (EI) m/z 184, 186 (M+). the solution was refluxed for 16 hours After concentration washed with sat'd aq. NaHCO3, H2O and brine The organic layer was dried over Na2SO4 concentrated

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

Procedure: A stirred mixture of 36.9 g of methyl o-chlorophenylacetate, 36.0 g of N-bromosuccinimide, and 2 drops of 48% hydrobromic acid in 500 ml of carbon tetrachloride is refluxed for 20 hours and then filtered through magnesium silicate. Evaporation under reduced pressure gives methyl α-bromo-o-chlorophenylacetate as a straw-colored liquid. is refluxed for 20 hours filtered through magnesium silicate Evaporation under reduced pressure

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

Procedure: To a solution of 10.0 g (59 mmol) (2-chlorophenyl)acetic acid in MeOH (10 mL) was added 9.6 mL (88 mmol) of trimethyl orthoformate and 0.32 mL (6.0 mmol) of H2SO4. The reaction was stirred at room temperature for 4 h then diluted with EtOAc and washed with H2O followed by a saturated aqueous solution of NaHCO3. The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure to provide 10.6 g (97%) of (2-chlorophenyl)-acetic acid methyl ester as a clear oil. The crude reaction product was not purified but used immediately. washed with H2O The organic phase was dried over anhydrous Na2SO4 concentrated under reduced pressure

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

Procedure: A solution of 2-chlorophenylacetic acid (10.0 g) in methanol (100 ml) containing 1 drop of concentrated sulphuric acid was heated at reflux for 2 hours. The reaction mixture was evaporated to half volume and partitioned between ethyl acetate (100 ml) and water (100 ml). The organic phase was dried over magnesium sulphate and evaporated to give the title compound (10.0 g) as a colourless oil. was heated at reflux for 2 hours The reaction mixture was evaporated to half volume partitioned between ethyl acetate (100 ml) and water (100 ml) The organic phase was dried over magnesium sulphate evaporated