Water → HCID 68380302, compound

Participants

Reaction Steps

Boron tribromide (19.1 mL, 198 mmol) was added to a −78° C. solution of 4-fluoro-1-methoxy-2-(1,1,1-trifluoropropan-2-yl)benzene (C43) (20.0 g, 90.0 mmol) in dichloromethane (400 mL). The cooling bath was removed and the reaction mixture was allowed to warm to room temperature over 66 hours. It was then cooled in an ice bath and treated drop-wise with water (50 mL) while venting into an aqueous potassium carbonate trap. When the vigorous reaction had subsided, additional water (300 mL) was added, and the mixture was stirred until all the solids had dissolved. The aqueous layer was extracted with dichloromethane (200 mL), and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure, while keeping the water bath between 23° C. and 35° C. The product was obtained as an oil, which contained some impurities by 1H NMR assessment; this was used without additional purification. Yield: 20.6 g, assumed quantitative. 1H NMR (400 MHz, CDCl3), product peaks only: δ 1.45 (d, J=7.4 Hz, 3H), 3.98-4.12 (m, 1H), 6.74 (dd, J=8.8, 4.5 Hz, 1H), 6.85-6.91 (m, 1H), 7.04-7.09 (m, 1H).

Provenance & Evidence