Boron tribromide → 3-[4-(4-Chlorophenoxy)-2-propylphenyl]-1-benzofuran-5-ol

HRID 1172815Notes

Reaction equation

HRID 1172815 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:17]4[CH:18]=[C:19]([O:22]C)[CH:20]=[CH:21][C:16]=4[O:15][CH:14]=3)=[C:9]([CH2:24][CH2:25][CH3:26])[CH:8]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:17]4[CH:18]=[C:19]([OH:22])[CH:20]=[CH:21][C:16]=4[O:15][CH:14]=3)=[C:9]([CH2:24][CH2:25][CH3:26])[CH:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 686903343-[4-(4-Chlorophenoxy)-2-propylphenyl]-5-methoxy-1-benzofuran

Product 1

HCID 574201423-[4-(4-Chlorophenoxy)-2-propylphenyl]-1-benzofuran-5-ol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from Step 10 (0.34 g, 0.86 mmol) in dichloromethane (5.0 mL) cooled with an ice bath was added boron tribromide (1.0 M in dichloromethane, 1.7 mL, 1.7 mmol). The reaction mixture was gradually warmed to room temperature over 1 h, diluted with ethyl acetate and poured into a saturated solution of sodium bicarbonate. The organic layer was washed with brine, dried and filtered through a short path of silica gel to give the title product.

Workup

  1. washThe organic layer was washed with brine
  2. customdried
  3. filtrationfiltered through a short path of silica gel

Sources & evidence

ORD record
ord-3e24c9d5ead049d1a14fa018759d0d9d
Source dataset
uspto-grants-2010_11
Patent number
US07834036B2

Reaction notes

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