177167-53-2

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

Procedure: To a stirred solution of 1,3-dichloro-5-iodobenzene (4.0 g, 14.6 mmol) in THF (30 mL), LDA (2.0 M in THF/heptane/ethylbenzene, 9.6 mL, 16.9 mmol) was added dropwise at −78° C. and stirred for 1 h at the same temperature. A solution of DMF (1.7 mL, 22.0 mmol) in THF (5 mL) was added slowly at −78° C. and stirred for 3 h. The reaction mixture was quenched with saturated NH4Cl (50 mL) and extracted with EtOAc (2×30 mL). The combined organic layers were washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 20% EtOAc/hexane as eluent) to afford compound A35-1 (1.4 g, 32%) as colorless oil. stirred for 3 h The reaction mixture was quenched with saturated NH4Cl (50 mL) extracted with EtOAc (2×30 mL) The combined organic layers were washed with water (50 mL), brine (50 mL) dried over anhydrous Na2SO4 concentrated under reduced pressure The crude product was purified by column chromatography (silica gel, 20% EtOAc/hexane as eluent) to afford compound A35-1 (1.4 g, 32%) as colorless oil

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

Procedure: To a stirred solution of 1,3-dichloro-5-iodobenzene (4.0 g, 14.6 mmol) in THF (30 mL), LDA (2.0 M in THF/heptane/ethylbenzene, 9.6 mL, 16.9 mmol) was added dropwise at −78° C. and stirred for 1 h at the same temperature. A solution of DMF (1.7 mL, 22.0 mmol) in THF (5 mL) was added slowly at −78° C. and stirred for 3 h. The reaction mixture was quenched with saturated NH4Cl (50 mL) and extracted with EtOAc (2×30 mL). The combined organic layers were washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 20% EtOAc/hexane as eluent) to afford compound A35-1 (1.4 g, 32%) as colorless oil. stirred for 3 h The reaction mixture was quenched with saturated NH4Cl (50 mL) extracted with EtOAc (2×30 mL) The combined organic layers were washed with water (50 mL), brine (50 mL) dried over anhydrous Na2SO4 concentrated under reduced pressure The crude product was purified by column chromatography (silica gel, 20% EtOAc/hexane as eluent) to afford compound A35-1 (1.4 g, 32%) as colorless oil