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

HRID 1028310

反応式

HRID 1028310 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 145293041,4-Dimethoxy-9H-carbazole収率 55%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
170 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-ed49843d2a5941e781b601c1a230fb14
出典データセット
uspto-grants-2014_05
特許番号
US08735440B2

関連ノート

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