Ethanethiol → 4-Bromo-2-methoxymethylbenzofuran-7-ol
Reaction equation
[H-].[Na+].C(S)C.[Br:6][C:7]1[C:12]2[CH:13]=[C:14]([CH2:16][O:17][CH3:18])[O:15][C:11]=2[C:10]([O:19]C)=[CH:9][CH:8]=1>CN(C)C=O>[Br:6][C:7]1[C:12]2[CH:13]=[C:14]([CH2:16][O:17][CH3:18])[O:15][C:11]=2[C:10]([OH:19])=[CH:9][CH:8]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 160 °C
Procedure
To a stirred solution of sodium hydride (334 mg, 60% in mineral oil) in dry N,N-dimethylformamide (25 ml) under an atmosphere of dry nitrogen at room temperature was added dropwise ethane thiol (0.586 ml). After stirring for 20 minutes a solution of 4-bromo-7-methoxy-2-methoxymethylbenzofuran (2.04 g) in N,N-dimethyl-formamide (7 ml) was added dropwise and the reaction mixture was heated at 160° C. for 2 hours. The reaction was cooled and the solvent removed in vacuo. The residue was dissolved in ethyl acetate (70 ml) and washed with ammonium chloride solution (70 ml). The organic extract was dried over magnesium sulphate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 50% ethyl acetate in hexane afforded the title compound as a white solid (1.21 g).
Workup
- additionwas added dropwise
- temperatureThe reaction was cooled
- customthe solvent removed in vacuo
- dissolutionThe residue was dissolved in ethyl acetate (70 ml)
- washwashed with ammonium chloride solution (70 ml)
- extractionThe organic extract
- dry with materialwas dried over magnesium sulphate
- filtrationfiltered
- customthe solvent removed in vacuo
- customPurification by column chromatography on silica eluting with 50% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-e7a2e65faf414c15a0bf90b4c4cad0af
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06331556B2
Reaction notes
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