P-Xylene → 3,5-Difluoro-4'-acetoxystilbene

HRID 78878

반응식

HRID 78878 반응식
CC1C=CC(C)=CC=1.[F:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([F:19])[CH:18]=1)[C:13](Cl)=O.[C:20]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=C)=[CH:26][CH:25]=1)(=[O:22])[CH3:21].CN1CCOCC1>CC([O-])=O.CC([O-])=O.[Pd+2].[Cl-].C(C1C=CC=C(C(C)C)C=1[NH+]1CCN(C2C(C(C)C)=CC=CC=2C(C)C)C1)(C)C.CCOC(C)=O>[C:20]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[CH:13][C:12]2[CH:11]=[C:10]([F:9])[CH:18]=[C:17]([F:19])[CH:16]=2)=[CH:26][CH:25]=1)(=[O:22])[CH3:21]

참가 물질

8

반응물 4

HCID 7809P-XyleneHCID 79724-MethylmorpholineHCID 758214-Ethenylphenyl acetateHCID 1456003,5-Difluorobenzoyl chloride

생성물 1

HCID 687421603,5-Difluoro-4'-acetoxystilbene수율 74.4%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 184547821,3-BIS(2,6-DIISOPROPYLPHENYL)imidazoLIDINIUM-CHLORIDE촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

A 25 mL round bottom flask was charged with p-xylene (10 mL), Pd(OAc)2 (11.3 mg, 0.05 mmol), 1,3-bis-(2,6-diisopropylphenyl)imidazolinium chloride (21.4 mg, 0.05 mmol), 3,5-difluorobenzoyl chloride (0.89 g, 5 mmol), 4-acetoxystyrene (0.97 g, 6 mmol), and N-methyl morpholine (0.69 g, 6 mmol). The mixture was stirred at 120° C. for 3.5 h under nitrogen atmosphere. Then it was cooled to room temperature and EtOAc was added and filtered. The filtrate was washed with brine and dried over Na2SO4. Then it was filtered and purified via flash chromatography and gave the product (1.02 g, 74%) as white solid. Data are: 1H NMR (CDCl3, 300 MHz) δ 7.51 (d, J=8.4 Hz, 2H), 7.12-6.97 (m, 6H), 6.70 (t, 1H), 2.31 (s, 3H).

후처리

  1. temperatureThen it was cooled to room temperature
  2. filtrationfiltered
  3. washThe filtrate was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationThen it was filtered
  6. custompurified via flash chromatography

출처 및 근거

ORD 기록
ord-999fdb07a7264857b0b22f06af7d7172
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841477B2

연결된 노트

불러오는 중…