Sodium Carbonate → HCID 117760182, 화합물

HRID 1049396노트

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HRID 1049396 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[F:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1B(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:17]([O:16][C:3]1[CH:4]=[C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:2]=1[C:26]1[CH:27]=[C:28]([O:31][CH3:32])[CH:29]=[CH:30][C:25]=1[F:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 41572112-Fluoro-5-methoxyphenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 128821681,1'-[(4-Bromo-1,3-phenylene)bis(oxymethylene)]dibenzene

생성물 1

HCID 117760182HCID 117760182, 화합물수율 90.3%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

Under an argon atmosphere, to a solution of (((4-bromo-1,3-phenylene)bis(oxy))bis(methylene))dibenzene (21.8 g) in toluene (160 mL) were added 2-fluoro-5-methoxyphenylboronic acid (13.8 g), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (2.23 g), tris(dibenzylideneacetone)dipalladium(0) (1.24 g) and 2.0 M aqueous sodium carbonate solution (81.0 mL), and the mixture was stirred at 80° C. for 14 hr. The reaction mixture was diluted with water, and filtered through celite. The filtrate was extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (22.1 g) as a pale-yellow oil.

후처리

  1. filtrationfiltered through celite
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washthe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-77cd6b080a0148dea8d021bff30c5beb
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382188B2

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