Toluene → HCID 71238684, 화합물

HRID 1502193노트

반응식

HRID 1502193 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(C)C=CC=CC=1>C(O)C>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:3][CH:4]=3

참가 물질

5

반응물 3

HCID 1140TolueneHCID 66827Phenylboronic AcidHCID 534010773,6-Dibromo-9-(4-methylphenyl)-9H-carbazole

생성물 1

HCID 71238684HCID 71238684, 화합물수율 51.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

3,6-Dibromo-N-(4-methylphenyl)carbazole (6.23 g) and phenylboronic acid (2.01 g) were added to a solvent mixture of toluene (60 mL) and ethanol (15 mL), followed by bubbling with nitrogen. Then, tetrakistriphenylphosphine palladium (290 mg) and 21.2% aqueous sodium carbonate solution (15.0 g) were added to the mixture, and the resultant mixture was refluxed under nitrogen flow for 5 hours. The mixture was diluted with toluene. The toluene layer was washed with water and dried and the toluene was evaporated. The residue was treated through silica gel column chromatography (eluent: toluene/hexane=1/4 (by mass)), to thereby obtain 3.20 g of 3-bromo-6-phenyl-N-(4-methylphenyl)carbazole as colorless powder.

후처리

  1. customby bubbling with nitrogen
  2. additionThen, tetrakistriphenylphosphine palladium (290 mg) and 21.2% aqueous sodium carbonate solution (15.0 g) were added to the mixture
  3. temperaturethe resultant mixture was refluxed under nitrogen flow for 5 hours
  4. additionThe mixture was diluted with toluene
  5. washThe toluene layer was washed with water
  6. customdried
  7. customthe toluene was evaporated
  8. additionThe residue was treated through silica gel column chromatography (eluent: toluene/hexane=1/4 (by mass))

출처 및 근거

ORD 기록
ord-575baa2aace94c44ad6a14d54e804c2f
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206202B2

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