Boron tribromide → 3-(4-Bromo-phenyl)benzofuran-6-ol

HRID 342209Notes

Reaction equation

HRID 342209 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17]C)=[CH:16][C:11]=3[O:10][CH:9]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:11]=3[O:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 109027443-(4-Bromo-phenyl)-6-methoxy-benzofuran

Product 1

HCID 545619733-(4-Bromo-phenyl)benzofuran-6-olYield 101.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.0 g of 3-(4-bromo-phenyl)-6-methoxy-benzofuran are treated at 0° C. with 100 ml of 1M boron tribromide solution in methylene chloride. The ice bath is removed and the reaction mixture is stirred, subsequently poured into saturated sodium carbonate solution and extracted with methylene chloride. The organic phases are washed with saturated sodium chloride solution, dried and evaporated. There are obtained 2.9 g of 3-(4-bromo-phenyl)-benzofuran-6-ol, MS: m/e 288 (M+, 1 Br).

Workup

  1. customThe ice bath is removed
  2. additionsubsequently poured into saturated sodium carbonate solution
  3. extractionextracted with methylene chloride
  4. washThe organic phases are washed with saturated sodium chloride solution
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-eae515a5a6f44a0280d0e37b30718af7
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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