Boron tribromide → Phenol, 2-amino-4-(methylsulfonyl)-
Reaction equation
C[O:2][C:3]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][C:4]=1[NH2:5].B(Br)(Br)Br>C(Cl)(Cl)Cl>[CH3:13][S:10]([C:7]1[CH:8]=[CH:9][C:3]([OH:2])=[C:4]([NH2:5])[CH:6]=1)(=[O:11])=[O:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound was prepared by reacting 2-methoxy-5-methylsulfonyl aniline (5.0 g, 24.8 mmol) with boron tribromide (26 mmol, 26 mL, 1M in dichloromethane) in chloroform (30 m L) at 0° C. After 20 minutes, the reaction was quenched with sodium bicarbonate and the ph of the aqueous phase was adjusted to pH 7 and extracted with ethyl acetate. Concentration under reduced pressure gave 690 mg of product as an orange solid (15%).
Workup
- customat 0° C
- customthe reaction was quenched with sodium bicarbonate
- extractionextracted with ethyl acetate
- concentrationConcentration under reduced pressure
Sources & evidence
- ORD record
- ord-76bc956b94ce4f85a0a5df5a37e12503
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08124602B2
Reaction notes
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