Toluene → Methyl 4-(5-cyano-7-isopropenyl-1,3-benzoxazol-2-yl)benzoate

HRID 2066829ノート

反応式

HRID 2066829 の反応式
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([O-:17])=[O:16])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=[C:4]([C:20]#[N:21])[CH:3]=1.[C:22]1(C)[CH:27]=CC=C[CH:23]=1.[C:29](=O)([O-])[O-].[Na+].[Na+].C(B(O)O)=CC(=C)C>C(O)C.O>[C:20]([C:4]1[CH:3]=[C:2]([C:22]([CH3:27])=[CH2:23])[C:10]2[O:9][C:8]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([O:17][CH3:29])=[O:16])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=1)#[N:21]

参加物

7

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 74788214HCID 74788214、化合物2 回HCID 86643502HCID 86643502、化合物2 回

生成物 1

HCID 68409145Methyl 4-(5-cyano-7-isopropenyl-1,3-benzoxazol-2-yl)benzoate

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
91 °C

実験手順

To a 5-l, 3-neck round-bottom flask fitted with a stirring paddle, a condenser blanketed with nitrogen, and a thermocouple, was added 4-(7-bromo-5-cyano-1,3-benzoxazol-2-yl)benzoate (55.5 g, INTERMEDIATE 35), toluene (2 l), water (375 ml), ethanol (150 ml), 2M aqueous sodium carbonate (250 ml), and isoprenylboronic acid (83.4 g, INTERMEDIATE 37). The mixture was purged with nitrogen three times and then tetrakis(triphenylphosphine)palladium(0) (9.1 g) was added, and the mixture was purged three times with nitrogen. The mixture was heated to reflux (91° C.) and stirred at this temperature overnight. The mixture was then cooled to 20° C. and the product was filtered, washed with water, dried, and transferred to a 3-l round-bottom flask and rinsed with toluene (1 l). Residual solvent was removed in vacuo. Mass spectrum (ESI) 319.1 (M+1).

後処理

  1. customThe mixture was purged with nitrogen three times
  2. additiontetrakis(triphenylphosphine)palladium(0) (9.1 g) was added
  3. customthe mixture was purged three times with nitrogen
  4. temperatureThe mixture was heated
  5. temperatureThe mixture was then cooled to 20° C.
  6. filtrationthe product was filtered
  7. washwashed with water
  8. customdried
  9. customtransferred to a 3-l round-bottom flask
  10. washrinsed with toluene (1 l)
  11. customResidual solvent was removed in vacuo

出典と根拠

ORDレコード
ord-5ed79b36660d488d9baa241091216cb2
出典データセット
uspto-grants-2012_10
特許番号
US08293721B2

反応ノート

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