2'-Bromoacetanilide → HCID 178474077, compound

Participants

Reaction Conditions

Reaction Steps

Following general procedure F using 2‐bromoacetanilide (53.5 mg, 0.25 mmol), B2pin2 (127 mg, 0.50 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and 1a (3.8 mg, 0.0075 mmol) in THF (1.25 mL). The reaction was stirred at 70 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internalstandard 1,2‐dimethoxyethane showed 1:1.4 meta:para borylation in 65% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1‐6:4) to give the title compound (as a 1:1.7:1.3 mixture of meta:para:SM ratio, as determined by 1 H NMR) as a colourless oil. NMR yields have been used for all comparisons.

Provenance & Evidence