Acetamide, N-[(2-chlorophenyl)methyl]-2,2,2-trifluoro- → HCID 178431063, compound

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Reaction Conditions

Reaction Steps

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 dtbpy (2.0 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 5:33:56 dimeta:meta:para borylation in 93% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1) to give the title compound (as a 4:33:66 mixture of dimeta:meta:para ratio, as determined by 1 H NMR) as a colourless oil (64 mg, 0.18 mmol, 70%). By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:

Provenance & Evidence