Boron tribromide → 5-Chloro-2-hydroxybenzene-1-sulfonamide

HRID 11662Notes

Reaction equation

HRID 11662 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12]C)=[C:6]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:7]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 132102965-Chloro-2-methoxybenzene-1-sulfonamide

Product 1

HCID 133217565-Chloro-2-hydroxybenzene-1-sulfonamideYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a suspension of 5-chloro-2-methoxy-benzenesulfonamide (0.52 g, 2.33 mmol) in dichloromethane (25 mL) at −78° C. was added boron tribromide (1M solution in dichloromethane, 3.5 mL, 3.5 mmol). The reaction was stirred at −78° C. for 30 minutes and then warmed to ambient temperature and stirred overnight. The reaction was quenched with water (0.30 mL) and the precipitate formed was removed by filtration. The filtrate was concentrated in vacuo and the crude product was purified by chromatography on silica gel to give the title compound (0.32 g).

Workup

  1. temperaturewarmed to ambient temperature
  2. stirringstirred overnight
  3. customThe reaction was quenched with water (0.30 mL)
  4. customthe precipitate formed
  5. customwas removed by filtration
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b01bc6866af44416bdc86c9e87868d5a
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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