Trifluoroacetic acid → 2-Fluoro-1-isopropyl-4-methoxybenzene

Participants

Reaction Steps

The solution of 2-(2-fluoro-4-methoxyphenyl)propan-2-ol in IPAC (500 ml, 451 mmol) and diphenyl sulfide (0.151 ml, 0.901 mmol) were combined in a hydrogenation shaker. The reaction mixture was purged with nitrogen/vacuum cycles, and 5% palladium on carbon (7.67 g, 1.802 mmol) was added, followed by TFA (17.36 ml, 225 mmol). Hydrogenation was conducted at 60° C. under 50 psig pressures for 12 h. The catalyst was removed by filtration through a 1 inch plug of Solka-Floc® powdered cellulose and rinsed with IPAC (49.8 ml). The filtrate was assayed and was found to contain 76 g of the desired product, which corresponds to a quantitative yield.

Provenance & Evidence