Water → HCID 67257850, compound
Reaction equation
[Br:1][C:2]1[S:3][C:4]([Br:13])=[CH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Li+].[CH3:15][CH:16]([N-]C(C)C)C.O1CC1.O>C1COCC1>[Br:13][C:4]1[S:3][C:2]([Br:1])=[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:5]=1[CH2:15][CH3:16]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -65 °C
Procedure
To a solution of 2,5-dibromo-3-phenylthiophene (2.54 g, 8.0 mmol) in dry THF (30 mL) at −65° C. was added LDA (8.8 mmol) dropwise. After stirring for 30 min at −65° C., oxirane (20.0 mmol) was added and the reaction was stirred for 2 h. The reaction mixture was then warmed to room temperature and water was added. The resulting mixture was extracted with EtOAc (3×100 mL), washed with brine, and dried over anhydrous Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the title compound.
Workup
- stirringthe reaction was stirred for 2 h
- temperatureThe reaction mixture was then warmed to room temperature
- extractionThe resulting mixture was extracted with EtOAc (3×100 mL)
- washwashed with brine
- dry with materialdried over anhydrous Na2SO4
- filtrationAfter filtration and concentration
- customthe crude product was purified by column chromatography
Sources & evidence
- ORD record
- ord-39eb8b49baed460d91e9b42f5f840ba0
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710245B2
Reaction notes
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