Cesium carbonate → Tert-butyl 4-(2,4-difluorophenyl)-2-nitrobenzoate

HRID 1673356노트

반응식

HRID 1673356 반응식
Cl[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([N+:15]([O-:17])=[O:16])[CH:3]=1.[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C1(C)C=CC=CC=1>[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([N+:15]([O-:17])=[O:16])[CH:3]=1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 27343342,4-Difluorophenylboronic acidHCID 63896832Tert-butyl 4-chloro-2-nitrobenzoate

생성물 1

HCID 67343403Tert-butyl 4-(2,4-difluorophenyl)-2-nitrobenzoate수율 48.7%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매HCID 1140Toluene용매

실험 절차

To 15 mL of toluene solution containing 1.5 g of tert-butyl 4-chloro-2-nitrobenzoate, 1.1 g of 2,4-difluorophenylboronic acid, 2.3 g of cesium carbonate, 27 mg of palladium acetate and 25 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl were added sequentially, and the resulting mixture was heated to reflux under nitrogen atmosphere for 8 hours. After the reaction mixture was cooled to room temperature, insoluble were removed by filtration and added a saturated sodium hydrogen carbonate aqueous solution. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10% citric acid aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue and a solid substance was separated by filtration to obtain 0.95 g of tert-butyl 4-(2,4-difluorophenyl)-2-nitrobenzoate as white solid.

후처리

  1. additionwere added sequentially
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux under nitrogen atmosphere for 8 hours
  4. custominsoluble were removed by filtration
  5. additionadded a saturated sodium hydrogen carbonate aqueous solution
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. washafter washed with 10% citric acid aqueous solution
  9. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  10. additionHexane and diisopropyl ether were added to the obtained residue
  11. customa solid substance was separated by filtration

출처 및 근거

ORD 기록
ord-f1b22ebecb064c74a735385689c4eec3
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07999132B2

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