Water → HCID 68380302, compound

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).

1. customThe cooling bath was removed
2. temperatureIt was then cooled in an ice bath
3. additiontreated drop-wise with water (50 mL)
4. customwhile venting into an aqueous potassium carbonate trap
5. customWhen the vigorous reaction
6. dissolutionhad dissolved
7. extractionThe aqueous layer was extracted with dichloromethane (200 mL)
8. dry with materialthe combined organic layers were dried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customthe water bath between 23° C. and 35° C
12. customThe product was obtained as an oil, which
13. customthis was used without additional purification

ORD record

ord-fc1985b8d29541819bdac99478304846

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067934B2