Water → 3-Bromo-7-methylphenanthrene

HRID 1084324노트

반응식

HRID 1084324 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[C:7](C(O)=O)[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[C:10]([CH3:16])[CH:9]=3.O>N1C2C(=CC=CC=2)C=CC=1.C1(C)C=CC=CC=1.C(Cl)Cl.C([O-])([O-])=O.O.O.[Cu].[Cu+2]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[CH:7][C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[C:10]([CH3:16])[CH:9]=3

참가 물질

6

반응물 2

HCID 962WaterHCID 151591353-Bromo-7-methyl-phenanthrene-9-carboxylic acid

생성물 1

HCID 151591363-Bromo-7-methylphenanthrene수율 103.1%

시약·촉매·용매 3

HCID 10922056HCID 10922056, 화합물촉매HCID 7047Quinoline용매HCID 21877217Toluene methylene chloride용매

실험 절차

A stirred mixture of 3-Bromo-7-methyl-phenanthrene-9-carboxylic acid (5.50 g, 17.5 mmol) and CuCO3.Cu(OH)2.H2O (1.5 g) in 50 ml of quinoline was rapidly heated to 210° C. Gas evolution was observed and the mixture became extremely dark. After 10 min the mixture was allowed to cool to room temperature and was diluted with PhCH3 --CH2Cl2 (9:1) and filtered. The filtrate was washed with 1N HCl (2x) and brine. Drying (Na2SO4) and evaporation gave 4.89 g of a brown oil which was flash chromatographed through 450 g of silica gel (10% CH2Cl2 /hexane) to yield 2.63 g (56%) of the title compound as a pale yellow solid.

후처리

  1. filtrationfiltered
  2. washThe filtrate was washed with 1N HCl (2x) and brine
  3. customDrying
  4. custom(Na2SO4) and evaporation

출처 및 근거

ORD 기록
ord-728b9f2bfb4c45baa25fb949851089fe
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05004740

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