Potassium Acetate → 3-Bromo-7-(acetoxymethyl)phenanthrene

HRID 1084316Notes

Reaction equation

HRID 1084316 reaction equation
[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]([CH2:16]Br)[CH:9]=3.[C:18]([O-:21])(=[O:20])[CH3:19].[K+]>CN(C=O)C.C(OCC)C>[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]([CH2:16][O:21][C:18](=[O:20])[CH3:19])[CH:9]=3

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 151591373-Bromo-7-(bromomethyl)-phenanthrene

Product 1

HCID 151591383-Bromo-7-(acetoxymethyl)phenanthreneYield 97%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-bromo-7-(bromomethyl)-phenanthrene (2.249 g, 6.425 mmol) and potassium acetate (1.26 g, 12.8 mmol) in 60 ml of DMF was heated at 80° C. for 7 hours. After cooling to RT, the reaction mixture was diluted with ethyl ether, washed with water and brine, dried (MgSO4) and evaporated to give 2.042 g (97%) of the title compound as a white solid which was used in the following reaction without purification.

Workup

  1. temperatureAfter cooling to RT
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-25df1000ce4a4e098b247d935aa1fbc5
Source dataset
uspto-grants-1991_04
Patent number
US05004739

Reaction notes

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