Toluene → HCID 68957047, 화합물

HRID 2191636노트

반응식

HRID 2191636 반응식
C1(C)C=CC=CC=1.Br[C:9]1[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:11]([N+:22]([O-:24])=[O:23])[CH:10]=1.[C:25](=[O:47])([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=1)[O:26][C:27]([CH3:30])([CH3:29])[CH3:28].C(=O)([O-])O.[Na+]>O.C(OCC)(=O)C.C(O)C>[C:27]([O:26][C:25]([O:31][C:32]1[CH:33]=[C:34]([C:9]2[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:11]([N+:22]([O-:24])=[O:23])[CH:10]=2)[CH:35]=[CH:36][CH:37]=1)=[O:47])([CH3:30])([CH3:28])[CH3:29]

참가 물질

8

반응물 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 27739553-(tert-Butoxycarbonyloxy)phenylboronic acid pinacol esterHCID 26369829tert-Butyl 4-bromo-2-nitrobenzoate

생성물 1

HCID 68957047HCID 68957047, 화합물수율 87.3%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매2회HCID 8857Ethyl Acetate용매

실험 절차

To toluene 24 mL solution of tert-butyl 4-bromo-2-nitrobenzoate 3.0 g were added ethanol 9.0 mL, water 4.5 mL, tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl carbonate 3.8 g, sodium hydrogen carbonate 2.1 g and tetrakis (triphenylphosphine)palladium(0) 0.57 g sequentially, and it was heated and refluxed under nitrogen atmosphere for 6 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added to it. After insoluble matter was filtrated, the organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=3:1] to give tert-butyl 4-(3-(tert-butoxycarbonyl)oxyphenyl)-2-nitrobenzoate 3.6 g of yellow oil.

후처리

  1. temperatureit was heated
  2. temperaturerefluxed under nitrogen atmosphere for 6 hours
  3. filtrationAfter insoluble matter was filtrated
  4. customthe organic layer was separated
  5. washafter washing with saturated sodium chloride aqueous solution
  6. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-65915fe6e6304aeea56777715bbbc788
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08327467B2

반응 노트

불러오는 중…