Hydrochloric Acid → 6-Bromo-3-(difluoromethoxy)-2-methoxyphenol

HRID 2171089Notes

Reaction equation

HRID 2171089 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]=1

Participants

4

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 6-Bromo-3-(difluoromethoxy)-2-methoxyphenol as a solid (800 mg, 93%).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with dichloromethane (3×)
  4. washThe combined dichloromethane layers were washed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ef8383dd011c4355af0e98e0e3cba7f3
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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