5-chloro-1-benzofuran-3-one

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

Procedure: According to the procedure of M. E. Jung et al., J. Org. Chem., 53, 423 (1988), a solution of diazomethane in ether [prepared from N-methyl-N-nitroso-p-toluenesulfonamide (5.8 g, 0.026 mol) and potassium hydroxide (2.9 g, 0.052 mol) in H2O (7 mL), ethanol (10 mL), and ether (70 mL) utilizing a mini-Diazald® apparatus] was added to 5-chloro-2-methoxybenzoyl chloride (2.0 g, 0.010 mol). The resulting mixture was stirred for 30 minutes, concentrated, and acetic acid (20 mL) was added. After 15 minutes, the mixture was concentrated to give 1.6 g (97%) of the product as an orange solid. concentrated acetic acid (20 mL) was added After 15 minutes the mixture was concentrated

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

Procedure: According to the procedure of M. E. Jung et al., J. Org. Chem., 53, 423 (1988), a solution of diazomethane in ether [prepared from N-methyl-N-nitroso-p-toluenesulfonamide (5.8 g, 0.026 mol) and potassium hydroxide (2.9 g, 0.052 mol) in H2O (7 mL), ethanol (10 mL), and ether (70 mL) utilizing a mini-Diazald® apparatus] was added to 5-chloro-2-methoxybenzoyl chloride (2.0 g, 0.010 mol). The resulting mixture was stirred for 30 minutes, concentrated, and acetic acid (20 mL) was added. After 15 minutes, the mixture was concentrated to give 1.6 g (97%) of the product as an orange solid. concentrated acetic acid (20 mL) was added After 15 minutes the mixture was concentrated

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

Procedure: According to the procedure of M. E. Jung et al., J. Org. Chem., 53, 423 (1988), a solution of diazomethane in ether [prepared from N-methyl-N-nitroso-p-toluenesulfonamide (5.8 g, 0.026 mol) and potassium hydroxide (2.9 g, 0.052 mol) in H2O (7 mL), ethanol (10 mL), and ether (70 mL) utilizing a mini-Diazald® apparatus] was added to 5-chloro-2-methoxybenzoyl chloride (2.0 g, 0.010 mol). The resulting mixture was stirred for 30 minutes, concentrated, and acetic acid (20 mL) was added. After 15 minutes, the mixture was concentrated to give 1.6 g (97%) of the product as an orange solid. concentrated acetic acid (20 mL) was added After 15 minutes the mixture was concentrated

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

Procedure: (Ref: J. Org. Chem. 1955; 20; 813-818) A solution of 2-chloro-1-(5-chloro-2-hydroxy-phenyl)-ethanone (5 g; 24.4 mmol) in ethanol was heated to reflux for 10 minutes and sodium acetate (2 g; 24.4 mmol) was added to the hot mixture. Mixture continued to reflux an additional 10 minutes, and reaction was stoppered and chilled to 0° C. for 20 minutes. Mixture was quenched with water and mixture extracted with ethyl acetate (3×75 mL). Combined organics was washed with brine and dried over MgSO4. Crude material was purified by chromatography using 0-1% methanol/DCM to afford 5-chlorobenzofuran-3-one as a oily solid. (3.0 g; 75% yield). to reflux for 10 minutes to reflux an additional 10 minutes reaction Mixture was quenched with water and mixture extracted with ethyl acetate (3×75 mL) Combined organics was washed with brine dried over MgSO4 Crude material was purified by chromatography

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

Procedure: A mixture of 5-chloro-benzofuran-3 (2H)-one (1.68 g, 10 mmol) and (carboxymethylene)triphenylphosphorane (5.22 g, 15 mmol) was refluxed in toluene (100 ml) for 48 hrs. At the end, reaction mixture was concentrated and loaded over silica-gel column. The column was eluted with hexane (500 ml) and later with 25% ethyl acetate. The product, ethyl(5-chloro-1-benzofuran-3-yl)acetate was obtained as a white oil. Yield: 1.8 g (75%); 239 (M+H). At the end, reaction mixture was concentrated The column was eluted with hexane (500 ml) and later with 25% ethyl acetate

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

Procedure: A mixture of 5-chloro-benzofuran-3 (2H)-one (1.68 g, 10 mmol) and (carboxymethylene)triphenylphosphorane (5.22 g, 15 mmol) was refluxed in toluene (100 ml) for 48 hrs. At the end, reaction mixture was concentrated and loaded over a silica-gel column. The column was eluted with hexane (500 ml) and later with 25% ethyl acetate. The product, ethyl(5-chloro-1-benzofuran-3-yl)acetate, was obtained as a white oil. Yield: 1.8 g (75%); 239 (M+H). At the end, reaction mixture was concentrated The column was eluted with hexane (500 ml) and later with 25% ethyl acetate

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

Procedure: (Ref: J. Org. Chem. 1955; 20; 813-818) A solution of 2-chloro-1-(5-chloro-2-hydroxy-phenyl)-ethanone (5 g; 24.4 mmol) in ethanol was heated to reflux for 10 minutes and sodium acetate (2 g; 24.4 mmol) was added to the hot mixture. Mixture continued to reflux an additional 10 minutes, and reaction was stoppered and chilled to 0° C. for 20 minutes. Mixture was quenched with water and mixture extracted with ethyl acetate (3×75 mL). Combined organics was washed with brine and dried over MgSO4. Crude material was purfied by chromatography using 0-1% methanol/DCM to afford 5-chlorobenzofuran-3-one as a oily solid. (3.0 g; 75% yield). to reflux for 10 minutes to reflux an additional 10 minutes reaction Mixture was quenched with water and mixture extracted with ethyl acetate (3×75 mL) Combined organics was washed with brine dried over MgSO4

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

Procedure: A mixture of 5-chloro-benzofuran-3 (2H)-one (1.68 g, 10 mmol) and (carboxymethylene)triphenylphosphorane (5.22 g, 15 mmol) was refluxed in toluene (100 ml) for 48 hrs. At the end, reaction mixture was concentrated and loaded over silica-gel column. The column was eluted with hexane (500 ml) and then with 25% ethyl acetate. The product, ethyl(5-chloro-1-benzofuran-3-yl)acetate, was obtained as a white oil. Yield: 1.8 g (75%); (M+H): 239. At the end, reaction mixture was concentrated The column was eluted with hexane (500 ml)

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

Procedure: According to the procedure of M. E. Jung et al., J. Org. Chem., 53, 423 (1988), a solution of diazomethane in ether [prepared from N-methyl-N-nitroso-p-toluenesulfonamide (5.8 g, 0.026 mol) and potassium hydroxide (2.9 g, 0.052 mol) in H2O (7 mL), ethanol (10 mL), and ether (70 mL) utilizing a mini-Diazald® apparatus] was added to 5-chloro-2-methoxybenzoyl chloride (2.0 g, 0.010 mol). The resulting mixture was stirred for 30 minutes, concentrated, and acetic acid (20 mL) was added. After 15 minutes, the mixture was concentrated to give 1.6 g (97%) of the product as an orange solid. concentrated acetic acid (20 mL) was added After 15 minutes the mixture was concentrated