Sodium methanethiolate → Methyl 2-(methylthio)-4-(trifluoromethyl)benzoate

HRID 10907

反応式

HRID 10907 の反応式
[CH3:1][S-:2].[Na+].[N+]([C:7]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])([O-])=O>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:1][S:2][C:7]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

参加物

6

反応物 2

HCID 4378561Sodium methanethiolateHCID 11276727Methyl 2-nitro-4-(trifluoromethyl)benzoate

生成物 1

HCID 10944828Methyl 2-(methylthio)-4-(trifluoromethyl)benzoate収率 103.9%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

Sodium thiomethoxide (91 mg; 1.3 mmol; 1.3 equiv) was dissolved in water (0.34 mL). Tetrabutylammonium bromide (48 mg; 0.15 mmol; 0.15 equiv) was added. Methyl 2-nitro-4trifluoromethylbenzoate (5a; 249 mg; 1.0 mmol) was dissolved in toluene and added to the mixture. The reaction mixture was stirred at ambient temperature for 1 h to completely consume 5a according to gas chromatography (GC) analysis. The reaction mixture was diluted with ethyl acetate and water and the layers were thoroughly mixed and then separated. The organic layer was dried over Na2SO4 and concentrated to afford 0.26 g of 6a which contained a small amount of tetrabutylammonium bromide. The crude product was filtered through a pad of flash silica gel to afford 226 mg (90%) of 6a.

後処理

  1. additionadded to the mixture
  2. customto completely consume 5a
  3. additionThe reaction mixture was diluted with ethyl acetate and water
  4. additionthe layers were thoroughly mixed
  5. customseparated
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-2c2a80a2d1154010aca22c7ac1ac6a93
出典データセット
uspto-grants-2006_08
特許番号
US07094919B2

関連ノート

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