Hydrogen Bromide → HCID 86708802, compound

4-Bromo-3-(difluoromethoxy)benzoic acid (6.65 mmol) was suspended in DCM (33 mL) and thionyl chloride (2.9 mL, 33 mmol) was added, followed by DMF (5 drops). After stirring at RT for 2 h, the reaction mixture was concentrated under reduced pressure. The crude residue was dissolved in DCM (17 mL) and treated with TMS-diazomethane (2.0 M in hexane, 8.3 mL, 16.6 mmol). After stirring at RT for 2 h, HBr (33% w/w in AcOH) (5.8 mL, 33 mmol) was added dropwise. After stirring for 1 h more at RT, the reaction mixture was concentrated under reduced pressure. The crude residue was diluted with EtOAc. The organic solution was washed with saturated aqueous NaHCO3 and brine, then dried over MgSO4, filtered and concentrated to afford 2-Bromo-1-(4-bromo-3-(difluoromethoxy)phenyl)ethanone (yield undetermined, material carried on crude assuming total conversion).

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. dissolutionThe crude residue was dissolved in DCM (17 mL)
3. stirringAfter stirring at RT for 2 h
4. stirringAfter stirring for 1 h more at RT
5. concentrationthe reaction mixture was concentrated under reduced pressure
6. additionThe crude residue was diluted with EtOAc
7. washThe organic solution was washed with saturated aqueous NaHCO3 and brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-1a8eb570b0f443cd86957fd11efb111f

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156823B2