N-bromobutanimide → HCID 59849199、化合物

HRID 604280ノート

反応式

HRID 604280 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 59849199HCID 59849199、化合物収率 124.2%

試薬・触媒・溶媒 2

HCID 6547Azobisisobutyronitrile触媒HCID 5943Carbon Tetrachloride溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2c0adc7b2d554140b2987c5172bf1f2c
出典データセット
uspto-grants-2011_03
特許番号
US07910585B2

反応ノート

読み込み中…