1,3-Dibromobenzene → 4-(3-bromophenyl)-N,N-dimethylmorpholine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,3-dibromobenzene (387 μL, 3.20 mmol), N,N-dimethylmorpholine-2-carboxamide (506 mg, 3.20 mmol), Pd2(dba)3 (73.3 mg, 0.0800 mmol), rac-BINAP (154 mg, 0.240 mmol) and NaOtBu (369 mg, 3.84 mmol) in toluene (8 mL) was heated at 80° C. for 5 hours under nitrogen. After cooling to room temperature, the mixture was diluted with DCM and filtered through a Celite pad. The combined filtrate and washings were concentrated. The residue was purified by silica gel column chromatography (EtOAc/hexane=95:5→90:10→80:20→67:33→50:50) to afford desired product (424 mg, 42.3%) as orange oil.

Provenance & Evidence