Benzo(B)Thiophene → Benzo[b]thiophen-2-yl(5-bromo-2-fluorophenyl)methanol
Reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2.C([Li])CCC.[Br:15][C:16]1[CH:17]=[CH:18][C:19]([F:24])=[C:20]([CH:23]=1)[CH:21]=[O:22]>O.O1CCCC1.CCCCCC>[S:1]1[C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[C:5]1[CH:21]([C:20]1[CH:23]=[C:16]([Br:15])[CH:17]=[CH:18][C:19]=1[F:24])[OH:22]Participants
Conditions
- Temperature
- -78 °C
Procedure
Into a tetrahydrofuran (20 ml) solution of benzo[b]thiophene (5.0 g) was dropwise added a n-hexane solution (25 ml) of n-butyl lithium (1.58 M) at −78° C. in an argon atmosphere, followed by stirring at −78° C. for 10 minutes. Into this solution was dropwise added a tetrahydrofuran (80 ml) solution of 5-bromo-2-fluorobenzaldehyde (8.0 g), followed by stirring at −78° C. for 2.5 hours. The temperature of the reaction mixture was elevated to room temperature. Water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 1-benzothien-2-yl(5-bromo-2-fluorophenyl)methanol (10.5 g, yield: 83.6%).
Workup
- stirringby stirring at −78° C. for 2.5 hours
- customwas elevated to room temperature
- extractionfollowed by extraction with ethyl acetate
- washThe organic layer was washed with a saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-5909da702ece48d4833fcec3ab628380
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198464B2
Reaction notes
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