Boron tribromide → 6-Bromo-2-fluoro-3-hydroxybenzaldehyde

A solution of 6-bromo-2-fluoro-3-methoxybenzaldehyde (2 g, 8.58 mmol) in dichloromethane (43 mL) under a nitrogen balloon was cooled to −78° C. in an acetone dry ice bath. 1 M boron tribromide solution in dichloromethane (9.5 mL) was added drop wise under nitrogen balloon. The reaction was stirred at room temperature overnight. The reaction was then put on an ice water bath and the excess boron tribromide was quenched with ice chips. Water was added and the solution was extracted with dichloromethane. The aqueous layer was extracted two times with dichloromethane. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure to give 6-bromo-2-fluoro-3-hydroxybenzaldehyde (1.61 g, 86% yield).

1. customThe reaction was then put on an ice water bath
2. customthe excess boron tribromide was quenched with ice chips
3. additionWater was added
4. extractionthe solution was extracted with dichloromethane
5. extractionThe aqueous layer was extracted two times with dichloromethane
6. washwashed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. customThe solvent was removed under reduced pressure

ORD record

ord-a6e9cfb14f5c417d846753de41535d88

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012431B2