Boron tribromide → 2-Amino-5-bromo-4-methylphenol
Reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([O:9]C)[C:5]([NH2:6])=[CH:4][C:3]=1[CH3:11].B(Br)(Br)Br>C(Cl)Cl>[NH2:6][C:5]1[CH:4]=[C:3]([CH3:11])[C:2]([Br:1])=[CH:8][C:7]=1[OH:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 4-bromo-6-methoxy-3-methylaniline (41) (500 mg, 2.3 mmol) in 6 ml DCM was added 1 M BBr3 in DCM (4.6 ml, 4.6 mmol). The reaction mixture was stirred at r.t. for 2 h, which turned to a brown solution and back to a brown suspension. After quenched with aq. sodium bicarbonate solution, the mixture was extracted with EA. The org. phase was washed with brine, dried over sodium sulfate, concentrated to dryness to give 581 mg 2-amino-5-bromo-4-methylphenol as dark oil.
Workup
- customAfter quenched with aq. sodium bicarbonate solution
- extractionthe mixture was extracted with EA
- washphase was washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-6e4edf1515d642fabb356a3131423ab6
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120751B2
Reaction notes
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