o-Chloroacetanilide → HCID 156594431, compound

Participants

Reaction Conditions

Reaction Steps

Following general procedure F using 2‐chloroacetanilide (42.4 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 50 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internalstandard 1,2‐dimethoxyethane showed 1:1.1 meta:para borylation in 74% 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 1:1.3:0.4 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