Boron tribromide → 2-Amino-4-(methylsulfonyl)phenol

HRID 255266Notes

Reaction equation

HRID 255266 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

HCID 25134Boron tribromideHCID 27595922-methoxy-5-methylsulfonylaniline

Product 1

HCID 73822-Amino-4-(methylsulfonyl)phenol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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

  1. customthe reaction was quenched with sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-dbf90b3439de4433bedd278b1445f003
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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