Benzene, 1,2-dichloro-4-iodo- → HCID 66763886, compound

Participants

Reaction Steps

To a solution of 3,4-dichloro-1-iodobenzene (1.33 g, 4.90 mmol) in tetrahydrofuran (10 mL) at room temperature, was added isopropylmagnesium bromide (2.4 mL of a 2.0 M solution in THF, 4.9 mmol) dropwise. After 2 h, a solution of 1-(3-methoxybenzyl)pyrrolidin-3-one (500 mg, 2.43 mmol) from Step B above in tetrahydrofuran (3 mL) was added dropwise at 0° C. The reaction mixture was warmed to ambient temperature and stirred for 2 h. The reaction mixture was quenched with saturated ammonium chloride (5 mL). The mixture was diluted with ethyl acetate (100 mL) and washed with saturated ammonium chloride (20 mL), water (20 mL), and brine (20 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by silica gel chromatography (5% ethyl acetate/methylene chloride to 80% ethyl acetate/methylene chloride) gave 3-(3,4-dichlorophenyl)-1-(3-methoxybenzyl)pyrrolidin-3-ol (500 mg, 58%) as a yellow oil: ESI MS (m/z) 352 [M+H]+.

Provenance & Evidence