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

HRID 22192

Reaction equation

HRID 22192 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 19736751HCID 19736751, compound

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 mole) 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). 1H NMR (CDCl3) δ: 7.28 (4H, m), 7.06 (4H, m), 4.13 (2H, m), 3.72 (1H, m), 3.55 (1H, m), 3.20 (1H, dd, J=6, 12 Hz), 1.21 (3H, t, J=6 Hz).

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-c5b877e7aced48708173e5628ebd3f82
Source dataset
uspto-grants-1995_06
Patent number
US05428027

Linked notes

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