Sodium hydride → 4-(2,6-Dimethyl-4-nitrophenoxy)-2-(4-fluorobenzenesulfonyl)phenol

HRID 1359166Notes

Reaction equation

HRID 1359166 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:12]=2[OH:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:22]1[C:27]([CH3:28])=[CH:26][C:25]([N+:29]([O-:31])=[O:30])=[CH:24][C:23]=1[CH3:32]>CN1C(=O)CCC1>[CH3:28][C:27]1[CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=[C:23]([CH3:32])[C:22]=1[O:17][C:15]1[CH:14]=[CH:13][C:12]([OH:18])=[C:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 99205692-Chloro-1,3-dimethyl-5-nitrobenzeneHCID 223448682-(4-Fluorobenzenesulfonyl)benzene-1,4-diol

Product 1

HCID 223448994-(2,6-Dimethyl-4-nitrophenoxy)-2-(4-fluorobenzenesulfonyl)phenol

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The title B compound, 2-(4-fluorobenzenesulfonyl)benzene-1,4-diol (1.2 g, 4.48 mmol) is added to a suspension of NaH (60% dispersion in mineral oil; 0.39 g, 9.86 mmol) in 15 mL of NMP at 0° C. in one portion. The mixture is warmed to RT and after 30 min, 4-chloro-3,5-dimethylnitrobenzene (1 g, 5.38 mmol) is added and the reaction is heated at 120° C. for 1 h. The reaction is cooled to RT and quenched with aqueous 1N HCl. The mixture is partitioned between water and EtOAc, and the organic solution is washed with water and brine, dried over anhydrous Na2SO4 and concentrated. Chromatography on silica (eluant; EtOAc/hexane-1/2/1/1) affords 4-(2,6-dimethyl-4-nitrophenoxy)-2-(4-fluorobenzenesulfonyl)phenol: NMR (CDCl3) 2.11 (s, 6H), 6.85-6.96 (m, 3H), 7.00 (app t, 2H, J=9), 7.88 (dd, 2H, J=9, 5), 7.98 (s, 2H), 8.73 (s, 1H).

Workup

  1. temperaturethe reaction is heated at 120° C. for 1 h
  2. temperatureThe reaction is cooled to RT
  3. customquenched with aqueous 1N HCl
  4. customThe mixture is partitioned between water and EtOAc
  5. washthe organic solution is washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-45e542e216eb4c18850b81b56b910128
Source dataset
uspto-grants-2003_07
Patent number
US06599942B1

Reaction notes

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