Toluene → HCID 59492872, 화합물

HRID 541131

반응식

HRID 541131 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH3:9].CC1(C)C(C)(C)OB([C:18]2[CH:28]=[CH:27][CH:26]=[CH:25][C:19]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])O1.C1(C)C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:18]2[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=[CH:27][CH:28]=2)=[C:3]([CH3:9])[CH:4]=1

참가 물질

6

반응물 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 844762-Bromo-5-chlorotolueneHCID 2773962Ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

생성물 1

HCID 59492872HCID 59492872, 화합물수율 99%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Under an argon atmosphere, a mixture of 2-bromo-5-chloro-toluene (20.55 g), ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (55.23 g), toluene (200 ml), water (125 ml), tripotassium phosphate (53.07 g) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride-dichloromethane complex (1.633 g) was stirred with heating under reflux for 1 hr. The reaction mixture was cooled to room temperature, activated carbon (1 g) was added and the mixture was stirred for 10 min at room temperature. The insoluble material was filtered off, and the filtrate was partitioned in a separatory funnel. The organic layer was washed twice with water, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=98/2) to give the title compound (27.20 g, 99%).

후처리

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hr
  3. additionactivated carbon (1 g) was added
  4. stirringthe mixture was stirred for 10 min at room temperature
  5. filtrationThe insoluble material was filtered off
  6. customthe filtrate was partitioned in a separatory funnel
  7. washThe organic layer was washed twice with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customthe obtained residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=98/2)

출처 및 근거

ORD 기록
ord-5f997e45d3144a3488a2ca99c79c64fc
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871934B2

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