Methyl Thioglycolate → Methyl {[bis(4-fluorophenyl)methyl]sulfanyl}acetate

HRID 1898946Notes

Reaction equation

HRID 1898946 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:13]([O:17][CH3:18])(=[O:16])[CH2:14][SH:15].[F:19][C:20]1[CH:34]=[CH:33][C:23]([CH:24](O)[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:22][CH:21]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:19][C:20]1[CH:21]=[CH:22][C:23]([CH:24]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[S:15][CH2:14][C:13]([O:17][CH3:18])=[O:16])=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 16907Methyl ThioglycolateHCID 1230494,4'-Difluorobenzhydryl alcoholHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 53981684Methyl {[bis(4-fluorophenyl)methyl]sulfanyl}acetateYield 50%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A slurry of ρ-toluenesulfonic acid monohydrate (108 mg, 0.57 mmol) and activated 3 Å molecular sieves (300-500 mg) in 4 mL of toluene is stirred for 15 minutes. Methyl thioglycolate (265 mg, 2.50 mmol ) is then added followed by 4,4'-difluoro-benzhydrol (Aldrich) (500 mg, 2.27 mmol). The reaction is stirred for 2.5 hours at room temperature followed by heating at 50°-60° C. for 45 minutes. The mixture is diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, brine and dried over magnesium sulfate. Chromatography on silica gel, eluting with a gradient of 10% ethyl acetate in hexane to 20% ethyl acetate in hexane, provides methyl [[bis-(4-fluorophenyl)methyl]thio]acetate as a yellow oil in 50% yield.

Workup

  1. temperatureby heating at 50°-60° C. for 45 minutes
  2. washwashed with saturated aqueous sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. washChromatography on silica gel, eluting with a gradient of 10% ethyl acetate in hexane to 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-42601431984f4e179b21b256158a30e1
Source dataset
uspto-grants-1996_11
Patent number
US05571825

Reaction notes

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