Boron tribromide → HCID 67338515, compound

HRID 1184536Notes

Reaction equation

HRID 1184536 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:28])/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][C:19]([S:22](=[O:25])(=[O:24])[NH2:23])=[C:18]([O:26]C)[CH:17]=2)[CH:9]=[CH:10][CH:11]=1>C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:28])/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][C:19]([S:22](=[O:25])(=[O:24])[NH2:23])=[C:18]([OH:26])[CH:17]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67338694HCID 67338694, compound

Product 1

HCID 67338515HCID 67338515, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (0.680 mL, 0.68 mmol) was added to a suspension of (E)-N-(3-chloro-phenyl)-3-(3-methoxy-4-sulfamoyl-phenyl)-acrylamide (0.045 g, 0.12 mmol) in dry DCM (12 mL) at 0° and under nitrogen atmosphere. The resulting mixture was allowed to reach RT, stirred at reflux temperature for 4 hrs and then poured into ice/water. The aqueous phase was concentrated under reduced pressure and the resulting residue was triturated with water, filtered and dried to give 13 mg of the title (E)-N-(3-chloro-phenyl)-3-(3-hydroxy-4-sulfamoyl-phenyl)-acrylamide as a white solid.

Workup

  1. customto reach RT
  2. temperatureat reflux temperature for 4 hrs
  3. concentrationThe aqueous phase was concentrated under reduced pressure
  4. customthe resulting residue was triturated with water
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-c490a21a2f434532b9870d6b4125b073
Source dataset
uspto-grants-2014_03
Patent number
US08669261B2

Reaction notes

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