Water → 3-Bromo-7-methylphenanthrene

HRID 1084314Notes

Reaction equation

HRID 1084314 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

HCID 151591363-Bromo-7-methylphenanthreneYield 103.1%

Reagents, catalysts & solvents 3

HCID 10922056HCID 10922056, compoundCatalystHCID 7047QuinolineSolventHCID 21877217Toluene methylene chlorideSolvent

Procedure

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 (2×) 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.

Workup

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

Sources & evidence

ORD record
ord-2447bbbad4af4dbdb4ec6e34b3d8a503
Source dataset
uspto-grants-1991_04
Patent number
US05004739

Reaction notes

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