Imidazole → 2-Bromo-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,5,6,7-tetrahydrobenzo[b]thiophene
Reaction equation
[Br:1][C:2]1[S:3][C:4]2[CH2:10][CH2:9][CH2:8][CH:7]([OH:11])[C:5]=2[CH:6]=1.N1C=CN=C1.[C:17]([Si:21]([CH3:24])([CH3:23])Cl)([CH3:20])([CH3:19])[CH3:18].O>CN(C)C=O>[Br:1][C:2]1[S:3][C:4]2[CH2:10][CH2:9][CH2:8][CH:7]([O:11][Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:24])[CH3:23])[C:5]=2[CH:6]=1Participants
Procedure
To a solution of 2-bromo-4,5,6,7-tetrahydro-1-benzothiophen-4-ol (5.0 g, 21 mmol) that was obtained in Example 8 (8a) in N,N-dimethylformamide (30 ml) were added successively imidazole (2.9 g, 43 mmol) and t-butyldimethylchlorosilane (3.5 g, 24 mmol) with stirring, and the resulting mixture was stirred for 2 hours. After stirring, the reaction mixture was poured into water (50 ml) to quench the reaction and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:9) as the eluent to afford the title compound (6.8 g) in a yield of 91% as a colourless oily product.
Workup
- stirringthe resulting mixture was stirred for 2 hours
- stirringAfter stirring
- customto quench
- customthe reaction
- extractionextracted with ether
- washThe extract was washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over magnesium sulfate
- filtrationAfter filtration
- customthe filtrate was evaporated in vacuo
Sources & evidence
- ORD record
- ord-d0a15647a0f54a7a852039e3ffbb147f
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687491B2
Reaction notes
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