Water → 2-(4-Hydroxy-2-methyl-phenyl)-benzo[b]thiophene-5-carboxylic acid ethyl ester

HRID 250246Notes

Reaction equation

HRID 250246 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:23]=[CH:22][C:9]2[S:10][C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][C:14]=3[CH3:21])=[CH:12][C:8]=2[CH:7]=1)=[O:5])[CH3:2].B(Br)(Br)Br.O.C(Cl)(=O)C>ClCCl.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:23]=[CH:22][C:9]2[S:10][C:11]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=3[CH3:21])=[CH:12][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 25134Boron tribromideHCID 574433392-(4-Methoxy-2-methyl-phenyl)-benzo[b]thiophene-5-carboxylic acid ethyl ester

Product 1

HCID 672715912-(4-Hydroxy-2-methyl-phenyl)-benzo[b]thiophene-5-carboxylic acid ethyl esterYield 43.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of 2-(4-Methoxy-2-methyl-phenyl)-benzo[b]thiophene-5-carboxylic acid ethyl ester (1.07 mmol; 350 mg) in anhydrous dichloromethane (4.00 mL) is added a 1 M solution of boron tribromide (1.29 mmol; 1.29 mL) in dichloromethane. The reaction mixture is stirred at room temperature for 4 h. Water and ethyl acetate are added. The aqueous layer is separated and the organic layer is dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue is dissolved in ethanol (5 mL) and acetyl chloride (3.48 mmol, 0.25 mL) is added. The mixture is stirred at reflux for 5 h. The solvent is removed under reduced pressure and the residue is chromatographed using a gradient of 5% ethyl acetate in hexane to 20% ethyl acetate in hexane to yield the title compound (145 mg, 40%) as a white solid. ES/MS m/e 313 (M+1).

Workup

  1. customThe aqueous layer is separated
  2. dry with materialthe organic layer is dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue is dissolved in ethanol (5 mL)
  6. stirringThe mixture is stirred
  7. temperatureat reflux for 5 h
  8. customThe solvent is removed under reduced pressure
  9. customthe residue is chromatographed

Sources & evidence

ORD record
ord-3fa41388b6094c20929339f3a5214a60
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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