Acetamide, N-[(2-chlorophenyl)methyl]-2,2,2-trifluoro- → HCID 178431060, compound

Temperature

35 °C

Following general procedure F using N‐(2‐chlorobenzyl)‐2,2,2‐trifluoroacetamide (59.4 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 35 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 10:76:15 dimeta:meta:para borylation in 100% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1) to give the title compound in two fractions, the first as a 4.2:1 mixture of meta:para ratio, as determined by 1 H NMR, as a white solid (42.5 mg, 0.12 mmol, 47%) and the second as a  10:75:12:21 mixture of dimeta:meta:para:B2pin2 ratio as determined by 1 H NMR, as a colourless oil (56.3 mg, 0.13 mmol). This gave the combined yield of 88.8 mg, 0.24 mmol, 97% as quoted.

ORD record

ord-c3f9f8b4a69448b88159732b4d1caea3

Source dataset

Borylation dataset from Roche

DOI

10.1002/anie.201708967