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

HRID 1006721ノート

反応式

HRID 1006721 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8fb707552037422d85c21d122d049226
出典データセット
uspto-grants-2004_09
特許番号
US06790978B2

反応ノート

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