Triethylamine → HCID 11535972, compound

Participants

Reaction Steps

A mixture of the 4-fluoro-3-nitroaniline (5.00 g, 32.03 mmol), phenylboronic acid (7.81 g, 64.05 mmol), copper(II) acetate (5.82 g, 32.03 mmol) and 4 Å molecular sieves (5.00 g) in dichloromethane (200.0 mL) and triethylamine (22.3 mL, 160 mmol) was placed in a round bottomed flask. The resulting suspension was stirred at room temperature under a dry ambient atmosphere for 48 h. The mixture was filtered through diatomaceous earth and the solvent was removed via rotary evaporation. The resulting residue was re-dissolved in EtOAc, adsorbed on silica gel and flash chromatographed (15% EtOAc/hexanes) to give 4-fluoro-3-nitro-N-phenylaniline as an orange solid (5.24 g, 70.5 % yield). M−, 231.

Provenance & Evidence