Acetic Acid → 3-aMino-5-(trifluoroMethyl)phenol
Reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([NH2:13])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Br.C(O)(=O)C>O>[NH2:13][C:5]1[CH:4]=[C:3]([OH:2])[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
To a round bottom flask was added 3-methoxy-5-trifluoromethyl-phenylamine (1.0 g, 5.23 mmol), 10 mL HBr (49% aq.), and 8 mL glacial acetic acid. A reflux condenser was attached and the solution heated to 140° C. for 20 h. The reaction was then diluted with water and neutralized to ˜pH 7 by slow addition of saturated NaHCO2. The aqueous solution was then extracted into EtOAc twice. The organic layers were combined, washed once with brine, dried over Mg2SO4, filtered, and concentrated in vacuo to yield the title compound as a tan solid (750 mg). MS (M+H)+=178; Calc'd 177.12 for C7H6F3NO.
Workup
- customA reflux condenser was attached
- extractionThe aqueous solution was then extracted into EtOAc twice
- washwashed once with brine
- dry with materialdried over Mg2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-0f766a72f2b84ad7848bb3beacd11583
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476434B2
Reaction notes
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