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

HRID 10907

반응식

HRID 10907 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2c2a80a2d1154010aca22c7ac1ac6a93
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094919B2

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