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Boron tribromide → (5-Chloro-2-hydroxyphenyl)methanesulfonamide

HRID 11669
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Reaction equation

HRID 11669 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:13]C)=[C:6]([CH2:8][S:9]([NH2:12])(=[O:11])=[O:10])[CH:7]=1.B(Br)(Br)Br>ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:13])=[C:6]([CH2:8][S:9]([NH2:12])(=[O:11])=[O:10])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21973342(5-Chloro-2-methoxyphenyl)methanesulfonamide

Product 1

HCID 21973532(5-Chloro-2-hydroxyphenyl)methanesulfonamideYield 86.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a suspension of (5-chloro-2-methoxy-phenyl)-methanesulfonamide (0.03 g, 0.13 mmol) in dichloroethane (1.5 mL) was added boron tribromide solution (1M in dichloromethane, 0.26 mL, 0.26 mmol). The reaction was stirred for one hour at ambient temperature. The reaction was quenched with water, saturated with sodium chloride and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated to give the title compound (0.025 g).

Workup

  1. customThe reaction was quenched with water, saturated with sodium chloride
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b4060db022494b248124cc4b060088c2
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07098212B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes