N,N-Dimethylaniline → [1,1'-Biphenyl]-4-yl carbonochloridate

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Reaction Steps

4-Hydroxybiphenyl (2.62 g, 15.4 mmol) in absolute toluene/diethyl ether (60/30 mL) was added dropwise in the space of 30 minutes, with ice cooling, to a solution of phosgene (1.98 g, 20 mmol) in absolute toluene (20 mL). Then, at −3° C., N,N-dimethylaniline (1.86 g, 1.95 mL, 15.4 mmol) in absolute toluene (10 mL) was added dropwise and it was stirred overnight, while slowly warming to room temperature. After cooling to 0° C. again, water (30 mL) was slowly added dropwise, then the organic phase was washed with 0.1N HCl, 0.1N NaOH and water (each 2×100 mL), dried over sodium sulphate and concentrated under vacuum.

Provenance & Evidence