Hydrochloric Acid → 6-Bromo-3-(difluoromethoxy)-2-methoxyphenol
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([F:11])[F:10])=[C:4]([O:12][CH3:13])[C:3]=1[O:14]COC.Cl>CO>[Br:1][C:2]1[C:3]([OH:14])=[C:4]([O:12][CH3:13])[C:5]([O:8][CH:9]([F:10])[F:11])=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a stirring solution of 1-bromo-4-(difluoromethoxy)-3-methoxy-2-(methoxymethoxy)benzene (1 g, 3.19 mmol) in methanol (15 mL) was added concentrated hydrochloride (2 mL) and the reaction mixture was heated to 50° C. for 1 h. The reaction mixture was cooled to RT, concentrated under reduced pressure and the obtained residue was basified with sodium bicarbonate solution and extracted with dichloromethane (3×). The combined dichloromethane layers were washed with brine, dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as a solid (800 mg, 93%).
Workup
- temperatureThe reaction mixture was cooled to RT
- concentrationconcentrated under reduced pressure
- extractionextracted with dichloromethane (3×)
- washThe combined dichloromethane layers were washed with brine
- dry with materialdried over sodium sulphate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-52dc51a924b54c9d8c3c20a2acf80d1c
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051290B2
Reaction notes
Loading…