N-[2-(2-bromophenyl)ethyl]-2,2,2-trifluoroacetamide → HCID 178431043, 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 dtbpy (2.0 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 1:1.7 meta:para borylation in 92% 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 1:1.8 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (103 mg). A small amount of B2Pin2 impurity was found to be inseparable from the final product on silica. Corrected yield ‐ 100 mg, 0.23 mmol, 94%. By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:

ORD record

ord-c948ea22cf6a42f39e7904366cf4bc1a

Source dataset

Borylation dataset from Roche

DOI

10.1002/anie.201708967