2,2,2-trifluoro-N-[2-(3-fluorophenyl)ethyl]acetamide → HCID 178431087, compound

Participants

Reaction Conditions

Reaction Steps

Following general procedure F using 4e (58.8 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). Stirred in vial at 50 °C for 20 hours. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 12.9:1 meta:para borylation in 98% yield (these numbers include some meta isomer that has also undergone NH borylation). The crude product was purified by silica gel chromatography (15% EtOAc in Petroleum Ether 40‐60 o C) which resulted in the cleavage of the N‐B bond in the NH‐borylation material and gave the title compound (as a 13:1 mixture of meta:para ratio, as determined by 1 H NMR) as a white solid (80 mg, 0.22 mmol, 89%).

Provenance & Evidence