Bromine → 1,2-Benzenediol, 4-bromo-3-fluoro- (9CI)
Reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[C:3]=1[OH:9].[Br:10]Br>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[Br:10][C:8]1[C:2]([F:1])=[C:3]([OH:9])[C:4](=[CH:6][CH:7]=1)[OH:5]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -10 °C
Procedure
3-Fluorocatechol (7.2 g) in 50 ml of carbon tetrachloride and 40 ml of chloroform are treated at -10° C. within 10 minutes with a solution of 2.88 ml of bromine in 30 ml of carbon tetrachloride. After stirring at -10° C. for 1 hour the reaction mixture is filtered. The residual solid is washed with a small amount of cold carbon tetrachloride and dried. There are obtained 6.30 g of 4-bromo-3-fluorocatechol as a white powder. This is treated with 6.0 ml of diphenylchloromethane and heated to 130° C. within 1 hour. Subsequently, the product is distilled at 135° C./0.05 Torr and recrystallized from ethanol. There are obtained 6.40 g of 5-bromo-4-fluoro-2,2-diphenyl-1,3-benzodioxol as a white crystalline powder of m.p. 61.5°-63° C.
Workup
- filtrationis filtered
- washThe residual solid is washed with a small amount of cold carbon tetrachloride
- customdried
Sources & evidence
- ORD record
- ord-87a04f41b5644a77b8d8dfbfc2297062
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05438052
Reaction notes
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