ethyl 2-bromo-4-chlorobenzoate

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2′-benzyloxybiphenyl boronic acid (50 mg, 0.16 mmol), ethyl 2-bromo-4-chlorobenzoate (66 mg, 0.25 mmol), potassium carbonate (88 mg, 0.64 mmol) and tetrakis(triphenylphosphine)palladium(0) (10 mg, 5 mol %) in 1:1 toluene/ethanol (2 ml) was stirred and heated at 90° C. under nitrogen for 12 hours. After cooling the mixture was diluted with diethyl ether and water and the organic phase dried (MgSO4) and evaporated to dryness. The residue was chromatographed with ethyl acetate/iso-hexane (1:9) to yield the title compound as a pale yellow gum. (46 mg, 66%). After cooling the mixture the organic phase dried (MgSO4) evaporated to dryness The residue was chromatographed with ethyl acetate/iso-hexane (1:9)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2′-benzyloxybiphenyl boronic acid (50 mg, 0.16 mmol), ethyl 2-bromo-4-chlorobenzoate (66 mg, 0.25 mmol), potassium carbonate (88 mg, 0.64 mmol) and tetrakis(triphenylphosphine)palladium(0) (10 mg, 5 mol %) in 1:1 toluene/ethanol (2 ml) was stirred and heated at 90° C. under nitrogen for 12 hours. After cooling the mixture was diluted with diethyl ether and water and the organic phase dried (MgSO4) and evaporated to dryness. The residue was chromatographed with ethyl acetate/iso-hexane (1:9) to yield the title compound as a pale yellow gum. (46 mg, 66%). After cooling the mixture the organic phase dried (MgSO4) evaporated to dryness The residue was chromatographed with ethyl acetate/iso-hexane (1:9)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromo-4-chlorobenzoic acid (235 mg, 1 mmol) and thionyl chloride (238 mg, 146 ul, 2 mmol) in toluene (5 ml) was heated at 90° C. for 1 hour. The reaction mixture was cooled and the solvent evaporated. The residue was dissolved in THF (1 ml) and treated with ethanol (1 ml). The solution was evaporated to dryness leaving the title compound as a yellow oil 263 mg 100% The reaction mixture was cooled the solvent evaporated The residue was dissolved in THF (1 ml) treated with ethanol (1 ml) The solution was evaporated to dryness

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromo-4-chlorobenzoic acid (235 mg, 1 mmol) and thionyl chloride (238 mg, 146 ul, 2 mmol) in toluene (5 ml) was heated at 90° C. for 1 hour. The reaction mixture was cooled and the solvent evaporated. The residue was dissolved in THF (1 ml) and treated with ethanol (1 ml). The solution was evaporated to dryness leaving the title compound as a yellow oil 263 mg 100% The reaction mixture was cooled the solvent evaporated The residue was dissolved in THF (1 ml) treated with ethanol (1 ml) The solution was evaporated to dryness

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2′-benzyloxybiphenyl boronic acid (50 mg, 0.16 mmol), ethyl 2-bromo-4-chlorobenzoate (66 mg, 0.25 mmol), potassium carbonate (88 mg, 0.64 mmol) and tetrakis(triphenylphosphine)palladium(0) (10 mg, 5 mol %) in 1:1 toluene/ethanol (2 ml) was stirred and heated at 90° C. under nitrogen for 12 hours. After cooling the mixture was diluted with diethyl ether and water and the organic phase dried (MgSO4) and evaporated to dryness. The residue was chromatographed with ethyl acetate/iso-hexane (1:9) to yield the title compound as a pale yellow gum. (46 mg, 66%). After cooling the mixture the organic phase dried (MgSO4) evaporated to dryness The residue was chromatographed with ethyl acetate/iso-hexane (1:9)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2′-benzyloxybiphenyl boronic acid (50 mg, 0.16 mmol), ethyl 2-bromo-4-chlorobenzoate (66 mg, 0.25 mmol), potassium carbonate (88 mg, 0.64 mmol) and tetrakis(triphenylphosphine)palladium(0) (10 mg, 5 mol %) in 1:1 toluene/ethanol (2 ml) was stirred and heated at 90° C. under nitrogen for 12 hours. After cooling the mixture was diluted with diethyl ether and water and the organic phase dried (MgSO4) and evaporated to dryness. The residue was chromatographed with ethyl acetate/iso-hexane (1:9) to yield the title compound as a pale yellow gum. (46 mg, 66%). After cooling the mixture the organic phase dried (MgSO4) evaporated to dryness The residue was chromatographed with ethyl acetate/iso-hexane (1:9)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromo-4-chlorobenzoic acid (235 mg, 1 mmol) and thionyl chloride (238 mg, 146 ul, 2 mmol) in toluene (5 ml) was heated at 90° C. for 1 hour. The reaction mixture was cooled and the solvent evaporated. The residue was dissolved in THF (1 ml) and treated with ethanol (1 ml). The solution was evaporated to dryness leaving the title compound as a yellow oil 263 mg 100% The reaction mixture was cooled the solvent evaporated The residue was dissolved in THF (1 ml) treated with ethanol (1 ml) The solution was evaporated to dryness

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2′-benzyloxybiphenyl boronic acid (50 mg, 0.16 mmol), ethyl 2-bromo-4-chlorobenzoate (66 mg, 0.25 mmol), potassium carbonate (88 mg, 0.64 mmol) and tetrakis(triphenylphosphine)palladium(0) (10 mg, 5 mol %) in 1:1 toluene/ethanol (2 ml) was stirred and heated at 90° C. under nitrogen for 12 hours. After cooling the mixture was diluted with diethyl ether and water and the organic phase dried (MgSO4) and evaporated to dryness. The residue was chromatographed with ethyl acetate/iso-hexane (1:9) to yield the title compound as a pale yellow gum. (46 mg, 66%). After cooling the mixture the organic phase dried (MgSO4) evaporated to dryness The residue was chromatographed with ethyl acetate/iso-hexane (1:9)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromo-4-chlorobenzoic acid (235 mg, 1 mmol) and thionyl chloride (238 mg, 146 ul, 2 mmol) in toluene (5 ml) was heated at 90° C. for 1 hour. The reaction mixture was cooled and the solvent evaporated. The residue was dissolved in THF (1 ml) and treated with ethanol (1 ml). The solution was evaporated to dryness leaving the title compound as a yellow oil 263 mg 100% The reaction mixture was cooled the solvent evaporated The residue was dissolved in THF (1 ml) treated with ethanol (1 ml) The solution was evaporated to dryness