Sodium Methoxide → Sodium 6-(2,4-difluorophenyl)naphthalene-2-sulfinate

HRID 735312Notes

Reaction equation

HRID 735312 reaction equation
C[O-].[Na+:3].[F:4][C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17]([S:22](CCC#N)(=[O:24])=[O:23])[CH:16]=[CH:15]2>O1CCCC1.CO.C(OCC)C>[F:4][C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17]([S:22]([O-:24])=[O:23])[CH:16]=[CH:15]2.[Na+:3]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 68900670HCID 68900670, compound

Product 1

HCID 68899091Sodium 6-(2,4-difluorophenyl)naphthalene-2-sulfinateYield 97.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Sodium methoxide (0.68 g, 12.6 mmol) was added to a solution of 3-{[6-(2,4-difluorophenyl)-2-naphthyl]sulfonyl}propanenitrile (Step 2, 4.04 g, 11.3 mmol) in tetrahydrofuran/methanol (1:1, 120 mL) and stirred at room temperature under nitrogen for 1 hour. The reaction mixture was diluted with diethyl ether (120 mL) and stirred for 30 minutes. The solid precipitate was collected by filtration to give sodium 6-(2,4-difluorophenyl)naphthalene-2-sulfinate (3.58 g). 1H NMR (500 MHz, CD3OD) δ 8.14 (1H, s), 8.03-7.97 (3H, m), 7.84 (1H, d, J=8.4 Hz), 7.66 (2H, dd, J=8.6, 20.2 Hz), 7.10-7.08 (2H, m).

Workup

  1. stirringstirred for 30 minutes
  2. filtrationThe solid precipitate was collected by filtration

Sources & evidence

ORD record
ord-7e634bd54ffb4d3c94c2f271e7f067f4
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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