HCID 68379851, compound → HCID 68380359, compound

Participants

Reaction Steps

4-Fluoro-1-methoxy-2-(3,3,3-trifluoroprop-1-en-2-yl)benzene (C42) (82 g, 370 mmol) was split into four batches; each batch was dissolved in methanol (200 mL), treated with 10% palladium on carbon (1 g, 10 mmol) and hydrogenated at 50 psi for 15 minutes. After careful filtration through Celite and rinsing of the filter pad with methanol, the four filtrates were combined and concentrated in vacuo, keeping the bath temperature at <25° C. The residue was dissolved in dichloromethane, filtered through Celite, and concentrated under reduced pressure, providing the product as a light yellow oil. Yield: 71.0 g, 320 mmol, 86%. 1H NMR (400 MHz, CDCl3) δ 1.42 (d, J=7.2 Hz, 3H), 3.83 (s, 3H), 4.06-4.19 (m, 1H), 6.84 (dd, J=9.0. 4.5 Hz, 1H), 6.98 (ddd, J=9.0, 7.8, 3.1 Hz, 1H), 7.06-7.11 (m, 1H).

Provenance & Evidence