Water → Methyl 4-bromo-2-((methylthio)methyl)benzoate

HRID 863400노트

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HRID 863400 반응식
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12]Br)[CH:3]=1.[CH3:14][S-:15].[Na+].O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12][S:15][CH3:14])[CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

생성물 1

HCID 18978023Methyl 4-bromo-2-((methylthio)methyl)benzoate수율 41.8%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
100 °C

실험 절차

A mixture of methyl 4-bromo-2-(bromomethyl)benzoate (12 g) and sodium thiomethoxide (2.5 g) in toluene was stirred at 100° C. for 2 hours. The mixture was then cooled, poured into water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried (anhydrous sodium sulphate) and evaporated to afford a brown oil which was purified by column chromatography on silica gel giving methyl 4-bromo-2-(methylsulphenylmethyl)benzoate (4.1 g) as white crystals, m.p. 79.3° C.

후처리

  1. temperatureThe mixture was then cooled
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (anhydrous sodium sulphate)
  6. customevaporated
  7. customto afford a brown oil which
  8. customwas purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-6df3e1d70f8b4c00bcc962cec833cca9
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05721193

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