Boron tribromide → 2-(4-Hydroxy-phenyl)-benzo[b]thiophene-6-carboxylic Acid Methyl Ester

HRID 424791Notes

Reaction equation

HRID 424791 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)[S:10][C:9]=2[CH:21]=1)=[O:4].B(Br)(Br)Br>ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[S:10][C:9]=2[CH:21]=1)=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 574432832-(4-Methoxy-phenyl)-benzo[b]thiophene-6-carboxylic acid methyl ester

Product 1

HCID 179625242-(4-Hydroxy-phenyl)-benzo[b]thiophene-6-carboxylic Acid Methyl EsterYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-methoxy-phenyl)-benzo[b]thiophene-6-carboxylic acid methyl ester (500 mg, 1.7 mmol) in dichloromethane (15 mL) at 0° C. is added BBr3 (4.2 mL, 1 M in dichloromethane). The reaction mixture is stirred at ambient temperature overnight. The reaction is quenched by the addition of methanol and concentrated under reduced pressure. The residue is partitioned between EtOAc and 1 N HCl. The organic layer is concentrated and the residue is purified via chromatography eluting with 0 to 25% EtOAc in hexanes to give the title compound (57 mg, 12%) as a tan solid. LC-ES/MS m/e 283 (M−1).

Workup

  1. customThe reaction is quenched by the addition of methanol
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is partitioned between EtOAc and 1 N HCl
  4. concentrationThe organic layer is concentrated
  5. customthe residue is purified via chromatography
  6. washeluting with 0 to 25% EtOAc in hexanes

Sources & evidence

ORD record
ord-9000870e3ec24c328b74d2c11ff2df36
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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