Methyl 2-[[(2,2,2-trifluoroacetyl)amino]methyl]benzoate → HCID 178497424, compound

Temperature

50 °C

Following general procedure F using methyl 2‐((2,2,2‐trifluoroacetamido)methyl)benzoate using (65.3 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 50 °C for 20 hours before cooling and the solventsremoved. Analysis of crude 1 H NMR using internalstandard 1,2‐dimethoxyethane showed 2.2:1 meta:para borylation in 88% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (9:1) to give the title compound (as a 2:1 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (81.2 mg, 0.21 mmol, 84%). By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:

ORD record

ord-dcc10e8b4fbf4b519fc38ff8991eb06b

Source dataset

Borylation dataset from Roche

DOI

10.1002/anie.201708967