N-[2-(2-bromophenyl)ethyl]-2,2,2-trifluoroacetamide → HCID 178431027, compound

Temperature

50 °C

Following general procedure F using 4f (74 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 8.0:1 meta:para borylation in 93% yield. The crude product was purified by silica gel chromatography (15% EtOAc in Petroleum Ether 40‐60 o C) gave the title compound (as a 7.2:1 mixture of meta:para ratio, as determined by 1 H NMR) as a white solid (103 mg). A small amount of B2Pin2 impurity was found to be inseparable from the final product on silica. Corrected yield ‐ 96 mg, 0.23 mmol, 91%.

ORD record

ord-cfea1f62d1754743bf73d823c2bbee3c

Source dataset

Borylation dataset from Roche

DOI

10.1002/anie.201708967