2,2,2-trifluoro-N-[[2-(trifluoromethyl)phenyl]methyl]acetamide → HCID 178431054, compound

Temperature

25 °C

Following general procedure F using 2,2,2‐trifluoro‐N‐(2‐(trifluoromethyl)benzyl)acetamide (67.8 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). The reaction was stirred at rt for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 13.1:1 meta:para borylation in 99% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (9:1‐7:3) to give the title compound in two fractions (as a 10:1:3.6 mixture of meta:para:B2pin2 ratio, as determined by 1 H NMR) as a colourless oil (83.0 mg, 0.17 mmol, 69%*) and (a >20:1 mixture of meta:para ratio, as determined by 1 H NMR and used for characterisation of the meta product) as an off white solid (20.5 mg, 0.05 mmol, 21%) giving a combined yield of 89.4 mg, 0.23 mmol, 90% as quoted.

ORD record

ord-c7db102c2b5d4294b118c8b962b51dec

Source dataset

Borylation dataset from Roche

DOI

10.1002/anie.201708967