4-Fluorobenzaldehyde → 1-(4-Fluorophenyl)-2-(4-(methylthio)phenyl)ethanol

HRID 741683Notes

Reaction equation

HRID 741683 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][S:11][C:12]1[CH:20]=[CH:19][C:15]([CH2:16][Mg]Cl)=[CH:14][CH:13]=1>C1COCC1>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH2:16][C:15]2[CH:19]=[CH:20][C:12]([S:11][CH3:10])=[CH:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 680234-FluorobenzaldehydeHCID 178503173HCID 178503173, compound

Product 1

HCID 194267921-(4-Fluorophenyl)-2-(4-(methylthio)phenyl)ethanolYield 24.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 4-fluorobenzaldehyde (70 mL, 660 mmol) in THF (150 mL) was added to a cold (-78° C.) solution of 4-(methylthio)benzylmagnesium chloride (660 mmol in 1 L of ether) (J.Org. Chem. 42, 19 14, 1977). The mixture was stirred at -78° C. for 10 min then warmed to 0° C. NH4OAc was added and the mixture was extracted with EtOAc. The EtOAc extracts were washed with brine, dried over MgSO4, filtered and concentrated to an oil. Chromatography of the oil on silica gel (eluted with 2.5 % EtOAc/toluene) gave 42 g of the title compound.

Workup

  1. temperaturethen warmed to 0° C
  2. extractionthe mixture was extracted with EtOAc
  3. washThe EtOAc extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-a619ec0114d4443b99ebce7fa4abbdaf
Source dataset
uspto-grants-1996_09
Patent number
US05552422

Reaction notes

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