Ammonium Chloride → (4-Bromo-thiophen-2-yl)-(4-ethyl-phenyl)-methanol
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=1.[CH2:9]([C:11]1[CH:16]=[CH:15][C:14]([Mg]Br)=[CH:13][CH:12]=1)[CH3:10].[Cl-].[NH4+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]([C:14]2[CH:15]=[CH:16][C:11]([CH2:9][CH3:10])=[CH:12][CH:13]=2)[OH:8])[S:5][CH:6]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-bromo-2-thiophenecarboxaldehyde (4.78 g) in tetrahydrofuran (40 ml) was cooled to 0° C. under argon atmosphere, and thereto was added dropwise 4-ethylphenylmagnesium bromide (0.5 M tetrahydrofuran solution, 50 ml). The mixture was stirred at the same temperature for 30 minutes, and thereto was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=97:3-84:16) to give 4-bromo-2-thienyl-4-ethylphenylmethanol (5.37 g) as colorless oil. APCI-Mass m/Z 279/281 (M+H—H2O). (2) The above 4-bromo-2-thienyl-4-ethylphenylmethanol was treated in a manner similar to Reference Example 1-(2) to give the target compound as colorless oil.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with brine
- dry with materialdried over magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=97:3-84:16)
Sources & evidence
- ORD record
- ord-850d355d3a764fc49dd4353dceb899b2
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202984B2
Reaction notes
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