Boron tribromide → 3-hydroxy-N,N-dimethylbenzenesulfonamide

HRID 902659Notes

Reaction equation

HRID 902659 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([S:13]([N:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])[CH:10]=[CH:11][CH:12]=1>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]([S:13]([N:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 14774741HCID 14774741, compound

Product 1

HCID 211278523-hydroxy-N,N-dimethylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of BBr3 (1 M in CH2Cl2, 2.0 mL, 2.0 mmol) was added dropwise to a −78° C. solution of 3-methoxy-N,N,-dimethyl-benzenesulfonamide (0.15 g, 0.7 mmol) in CH2Cl2 (2 mL). The mixture was warmed to rt and stirred for 2 h, then cooled to 0° C. and quenched with saturated NaCO3. The aqueous phase was neutralized with saturated NH4Cl and extracted with EtOAc. The organic extracts were washed with brine, dried (MgSO4), filtered and concentrated to give an oil which was directly in the next step. MS (ESI) 202 (M+H+).

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with saturated NaCO3
  3. extractionextracted with EtOAc
  4. washThe organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an oil which

Sources & evidence

ORD record
ord-6270a09b90ab4682abb56addb47182cc
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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