2-Chloroaniline → 1,4-Dimethoxy-9H-carbazole

HRID 1028310

반응식

HRID 1028310 반응식
CC([O-])(C)C.[Na+].Cl[C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10].Br[C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[O:24][CH3:25]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:25][O:24][C:17]1[C:16]2[NH:10][C:9]3[C:8](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:21]=2[C:20]([O:22][CH3:23])=[CH:19][CH:18]=1

참가 물질

6

반응물 3

HCID 72402-ChloroanilineHCID 91353Benzene, 2-bromo-1,4-dimethoxy-HCID 23676156Sodium t-butoxide

생성물 1

HCID 145293041,4-Dimethoxy-9H-carbazole수율 55%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

반응 조건

온도
170 °C

실험 절차

Following a published procedure (Bedford, R. B.; Betham, M. J. Org. Chem. 2006, 71, 9403-9410), NaOtBu (0.754 g, 7.84 mmol), Pd(OAc)2 (0.014 g, 0.06 mmol), and [HPtBu3][BF4](0.023 g, 0.078 mmol) were suspended in dry toluene (5 mL) in a microwave vial. 2-Chloroaniline (0.165 mL, 1.567 mmol) and 2-bromo-1,4-dimethoxybenzene (0.240 mL, 1.598 mmol) were then added, and the vial was sealed. The reaction was then heated in the microwave reactor at 170° C. for 4 h, allowed to cool, and then quenched by addition of 1M HCl. The aqueous phase was extracted with CH2Cl2, the organic layer was dried over Na2SO4, filtered and condensed. The crude mixture was purified by chromatography (SiO2, 0-10% EtOAc/Hexane) to afford the title product (0.193 g, 55%).

후처리

  1. customthe vial was sealed
  2. temperatureto cool
  3. customquenched by addition of 1M HCl
  4. extractionThe aqueous phase was extracted with CH2Cl2
  5. dry with materialthe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customcondensed
  8. customThe crude mixture was purified by chromatography (SiO2, 0-10% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-ed49843d2a5941e781b601c1a230fb14
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735440B2

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