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

HRID 2093582노트

반응식

HRID 2093582 반응식
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]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 74788214HCID 74788214, 화합물2회HCID 86643502HCID 86643502, 화합물2회

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
91 °C

실험 절차

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 1) toluene (2 l), water (375 ml), ethanol (150 ml), 2M aqueous sodium carbonate (250 ml), and isoprenylboronic acid (83.4 g, INTERMEDIATE 3). 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).

후처리

  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

출처 및 근거

ORD 기록
ord-d9d045efc71246a7886de28a8eee081e
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445480B2

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