Benzo(B)Thiophene → (1-Benzothien-2-yl)(5-bromo-2-methoxyphenyl)methanol
Reaction equation
CCCCCC.[S:7]1[CH:11]=[CH:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]1=2.[Br:16][C:17]1[CH:18]=[CH:19][C:20]([O:25][CH3:26])=[C:21]([CH:24]=1)[CH:22]=[O:23].[Cl-].[NH4+]>O1CCCC1>[S:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH:10]=[C:11]1[CH:22]([C:21]1[CH:24]=[C:17]([Br:16])[CH:18]=[CH:19][C:20]=1[O:25][CH3:26])[OH:23]Participants
Procedure
1.6 M n-butylithium hexane solution (30.5 mL) was added to a mixture of benzo[b]thiophene (6.6 g, 0.049 mol) and tetrahydrofuran (66 mL) at −78° C. After stirred for 0.5 hours, the reaction mixture was added with a tetrahydrofuran (50 mL) solution of 5-bromo-2-methoxybenzaldehyde (10.0 g, 0.047 mol), further stirred for five minutes and warmed to room temperature. After the reaction mixture was added with a saturated ammonium chloride aqueous solution and extracted with ethyl acetate, the organic phase was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain pale yellow crystal (1-benzothien-2-yl)(5-bromo-2-methoxyphenyl)methanol (11.3 g, 69%).
Workup
- stirringfurther stirred for five minutes
- extractionextracted with ethyl acetate
- washthe organic phase was washed with brine
- dry with materialdried with anhydrous magnesium sulfate
- filtrationAfter the desiccant was filtered off
- customthe residue obtained
- customby evaporating the solvent under reduced pressure
- customwas purified by silica gel column chromatography (hexane:ethyl acetate=6:1)
Sources & evidence
- ORD record
- ord-ccbbada91da44e169dd5a474d4d54c05
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08017792B2
Reaction notes
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