N-bromobutanimide → Methyl 2-(4-(bromomethyl)phenyl)-2-methylpropanoate

HRID 1282116노트

반응식

HRID 1282116 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 13296592Methyl 2-methyl-2-(4-methylphenyl)propanoate

생성물 1

HCID 18423131Methyl 2-(4-(bromomethyl)phenyl)-2-methylpropanoate수율 97%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

A solution of methyl 2-(4-methylphenyl)-2-methylpropionate (58.5 g), N-bromosuccinimide (54.2 g), benzoyl peroxide (1.2 g) and carbon tetrachloride (300 ml) was refluxed for 40 min. After being cooled, the reaction mixture was filtrated. The filtrate was washed with an aqueous sodium sulfite solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give methyl 2-(4-bromomethylphenyl)-2-methylpropionate (80.0 g) as a pale-brown oil. To a solution of this oil in dimethylformamide (500 ml) was added sodium azide (21.14 g) and the mixture was stirred at 80° C. for 40 min. The reaction mixture was poured into water (1000 ml) and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (developing solvent; hexane,hexane:ethyl acetate=20:1) to give the title compound (48.1 g) as a pale-yellow oil.

후처리

  1. temperatureAfter being cooled
  2. filtrationthe reaction mixture was filtrated
  3. washThe filtrate was washed with an aqueous sodium sulfite solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-5af9b9114fa145e5b3381116fff266d8
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06455528B1

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