2-Fluorothiophenol → Ethyl 4-fluoro-alpha-[[(2-fluorophenyl)thio]methyl]benzeneacetate

HRID 1646985

Reaction equation

HRID 1646985 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[SH:22].[O-]CC.[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:14][S:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[F:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 5202162-FluorothiophenolHCID 2723922Sodium ethoxideHCID 19736751Ethyl 2-(4-fluorophenyl)acrylate

Product 1

HCID 19927552Ethyl 4-fluoro-alpha-[[(2-fluorophenyl)thio]methyl]benzeneacetateYield 82.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The crude product from Step A (3.9 g, 20 mmole) was taken up in 20 ml of ethanol. To this solution, being stirred at room temperature, was added 2-fluorothiophenol (2.5 g, 20 mmole) and 50 mg of solid sodium ethoxide. After stirring for eight hours the ethanol was concentrated and the residue taken up in ether. The ether mixture was washed twice with 15% NaOH solution, dried (MgSO4) and concentrated to a colorless oil (5.3 g, 82% yield).

Workup

  1. concentrationwas concentrated
  2. washThe ether mixture was washed twice with 15% NaOH solution
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-ae3ef02d26014c06b8231c688f6a2538
Source dataset
uspto-grants-1993_01
Patent number
US05182303

Linked notes

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