Hydrogen Bromide → 4-Bromo-2-chloro-1-(trifluoromethoxy)benzene
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]([F:13])([F:12])[F:11])N.N([O-])=O.[Na+].[BrH:18]>C(O)(=O)C.S(=O)(=O)(O)O.O.[Cu]Br>[Cl:1][C:2]1[CH:3]=[C:4]([Br:18])[CH:6]=[CH:7][C:8]=1[O:9][C:10]([F:13])([F:12])[F:11]Participants
8
Reactant 3
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 50 °C
Procedure
A solution of 3-chloro4-trifluoromethoxyaniline (5.1 g) in acetic acid (31 ml) was stirred and treated with sodium nitrite (2.16 g) in concentrated sulphuric acid (14 ml) at below 18° C. After an additional 1 hour at 10° C., the solution was added to a mixture of copper (I) bromide (7.7 g) and hydrobromic acid (24.5 ml) in water at 40-50° C. The reaction was completed by heating at 50° C. for 2 hours, water was added and the mixture filtered. The filtrate was extracted with ether, washed with sodium bicarbonate, dried (magnesium sulphate) and evaporated to give 3-chloro-4-trifluoromethoxy-bromobenzene (6.05 g) as a brown oil, NMR (CDCl3) 7.10(m,1H), 7.35(m,1H), 7.55(d,1H).
Workup
- filtrationthe mixture filtered
- extractionThe filtrate was extracted with ether
- washwashed with sodium bicarbonate
- dry with materialdried (magnesium sulphate)
- customevaporated
Sources & evidence
- ORD record
- ord-51393b3102274429b829dd5655f121b0
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06323155B1
Reaction notes
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