3-Fluoro-N-trifluoroacetylbenzylamine → HCID 178431089, compound

Participants

Reaction Conditions

Reaction Steps

Following general procedure F using 2,2,2‐trifluoro‐N‐(3‐fluorobenzyl)acetamide (55.3 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 solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 1.5:1 meta:para borylation in 53% yield. The crude product wassubjected to silica gel chromatography (Pet. Ether (40‐60):EtOAc (9:1) however significant decomposition was observed. A small para enriched fraction (1:2.7 meta:para isomerration by 1 H NMR)wasisolated as an off white solid (8 mg, 0.02 mmol, 9%). By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:

Provenance & Evidence