Reaction equation
[H-].[Li+].[Cl:3][C:4]1[CH:5]=[C:6]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH:7]=[C:8]([Cl:10])[CH:9]=1.[Br:17][C:18]1[CH:19]=[C:20]([C:24](=[O:26])[CH3:25])[S:21][C:22]=1[CH3:23].C(OC)(C)(C)C>C1COCC1>[Br:17][C:18]1[CH:19]=[C:20]([C:24](=[O:26])[CH2:25][C:11]([C:6]2[CH:5]=[C:4]([Cl:3])[CH:9]=[C:8]([Cl:10])[CH:7]=2)([OH:16])[C:12]([F:13])([F:14])[F:15])[S:21][C:22]=1[CH3:23]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
LiH (3.2 g) is added to a solution of 1-(3,5-dichloro-phenyl)-2,2,2-trifluoro-ethanone (56 g) and 1-(4-bromo-5-methyl-thiophen-2-yl)-ethanone (41 g) in dry THF (500 ml). After 5 h at 60° C. under nitrogen atmosphere, tert-butylmethylether (500 ml) is added to the reaction mixture. The reaction is slowly quenched with water (500 ml) at 5° C. and further extracted twice with tert-butylmethylether (500 ml). The organic phases are combined, washed with a saturated aqueous solution of NaCl, dried over MgSO4 and concentrated in vacuo to yield 1-(4-bromo-5-methyl-thiophen-2-yl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-butan-1-one (110 g, 77% purity) as a brown oil. The crude product is used without further purification.
Workup
- customThe reaction is slowly quenched with water (500 ml) at 5° C.
- extractionfurther extracted twice with tert-butylmethylether (500 ml)
- washwashed with a saturated aqueous solution of NaCl
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-256f1e9a4bc240aaa0a54cd7126c754c
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822466B2
Linked notes
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