N-bromobutanimide → HCID 59849199, 화합물

HRID 604280노트

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HRID 604280 반응식
[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C:5]=1[CH3:21].[Br:23]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([O:13][Si:14]([C:17]([CH3:18])([CH3:19])[CH3:20])([CH3:15])[CH3:16])[C:5]=1[CH2:21][Br:23]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 598491603-(Tert-butyl-dimethyl-silanyloxy)-2-methyl-6-nitro-benzoic acid methyl ester

생성물 1

HCID 59849199HCID 59849199, 화합물수율 124.2%

시약·촉매·용매 2

HCID 6547Azobisisobutyronitrile촉매HCID 5943Carbon Tetrachloride용매

반응 조건

온도
80 °C

실험 절차

To a solution of 3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-nitro-benzoic acid methyl ester (8.9 g, 25.1 mmol) and N-bromosuccinimide (5.36 g, 30.1 mmol) in 50 mL of CCl4 is added 2,2′-azobisisobutyronitrile (412 mg, 2.5 mmol) at room temperature. The reaction mixture is stirred at 80° C. for 22 hours and then cooled to room temperature and then quenched by crushed ice. The mixture is extracted with dichloromethane and washed with aqueous NaHCO3 solution followed by brine, dried over Na2SO4, filtered and evaporated in vacuo to afford the 2-bromomethyl-3-(tert-butyl-dimethyl-silanyloxy)-6-nitro-benzoic acid methyl ester (12.6 g) as brown oil. 1H-NMR (400 MHz, δ, ppm) CDCl3: 0.37 (s, 6H), 1.07 (s, 9H), 4.0 (s, 3H), 4.49 (s, 2H), 6.94 (d, 1H), 8.09 (d, 1H).

후처리

  1. temperaturecooled to room temperature
  2. customquenched
  3. customby crushed ice
  4. extractionThe mixture is extracted with dichloromethane
  5. washwashed with aqueous NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-2c0adc7b2d554140b2987c5172bf1f2c
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910585B2

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