4-(Ethylthio)benzaldehyde → [2-(Benzyloxy)-5-(trifluoromethyl)phenyl][4-(ethylthio)phenyl]methanol

HRID 1945190Notes

Reaction equation

HRID 1945190 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:25]([S:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=[O:33])=[CH:30][CH:29]=1)[CH3:26]>C(OCC)C>[CH2:18]([O:17][C:8]1[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]=1[CH:32]([C:31]1[CH:34]=[CH:35][C:28]([S:27][CH2:25][CH3:26])=[CH:29][CH:30]=1)[OH:33])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 70066544-(Ethylthio)benzaldehydeHCID 187826691-(Benzyloxy)-2-bromo-4-(trifluoromethyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 86659305[2-(Benzyloxy)-5-(trifluoromethyl)phenyl][4-(ethylthio)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of butyl lithium (1.6M in hexane, 1.03 ml) was added to a stirred solution of the product from step (i) (0.5 g) in diethylether (20 ml) at −78° C. After 1 h, 4-ethylsulfanyl-benzaldehyde (0.25 g) was added and stirred for a further 1 h. The reaction was quenched with water, extracted with diethylether and the organic layer dried, then evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 50% diethylether/isohexane. Yield 0.7 g

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with diethylether
  3. customthe organic layer dried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by chromatography on silica eluting with 50% diethylether/isohexane

Sources & evidence

ORD record
ord-8e8bd116d24e45ccbefe80c13b7f90e4
Source dataset
uspto-grants-2013_03
Patent number
US08394986B2

Reaction notes

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