tert-Butyl methyl ether → 1-(5-Bromo-4-methyl-thiophen-2-yl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-butan-1-one

HRID 390767Notes

Reaction equation

HRID 390767 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[S:22][C:21]([C:23](=[O:25])[CH3:24])=[CH:20][C:19]=1[CH3:26].CC(OC)(C)C>C1COCC1>[Br:17][C:18]1[S:22][C:21]([C:23](=[O:25])[CH2:24][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])=[CH:20][C:19]=1[CH3:26]

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 62714Lithium hydrideHCID 27582311-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-oneHCID 454803531-(5-Bromo-4-methylthiophen-2-yl)ethan-1-one

Product 1

HCID 866580381-(5-Bromo-4-methyl-thiophen-2-yl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-butan-1-oneYield 111.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiH (2.06 g) is added to a solution of 3′,5′-dichloro-2,2,2-trifluoroacetophenone (48.0 g) and 1-(5-bromo-4-methyl-thiophen-2-yl)-ethanone (30.3 g) in THF (1000 ml). After 2 hours at 60° C. MTBE is added (300 ml) and the reaction mixture is poured onto water (500 ml) at 0° C. The organic phase is extracted with water and a saturated aqueous solution of NaCl, dried over Na2SO4 and concentrated in vacuo to yield 71.2 g of 1-(5-bromo-4-methyl-thiophen-2-yl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-hydroxybutan-1-one. The crude product is used without further purification.

Workup

  1. additionthe reaction mixture is poured onto water (500 ml) at 0° C
  2. extractionThe organic phase is extracted with water
  3. dry with materiala saturated aqueous solution of NaCl, dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69c159e3c01b4a2aa65b81fe1b2c91d9
Source dataset
uspto-grants-2013_02
Patent number
US08383659B2

Reaction notes

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