Ethyl 3-(4-bromo-2-hydroxyphenyl)-3-oxopropanoate → 7-Bromo-4-hydroxycoumarin

HRID 1988889Notes

Reaction equation

HRID 1988889 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][C:10]([O:12]CC)=O)=[C:4]([OH:16])[CH:3]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:8]([OH:15])=[CH:9][C:10](=[O:12])[O:16]2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 59127384Ethyl 3-(4-bromo-2-hydroxyphenyl)-3-oxopropanoate2×

Product 1

HCID 546962297-Bromo-4-hydroxycoumarinYield 78.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl 3-(4-bromo-2-hydroxyphenyl)-3-oxopropanoate (Intermediate 30) (2.0 g) in dry toluene (20 ml) was stirred at reflux under nitrogen for 24 h. On cooling the resulting precipitate was collected by filtration, washed with ether and dried to give the title compound as a white solid (1.32 g).

Workup

  1. temperatureat reflux under nitrogen for 24 h
  2. temperatureOn cooling the resulting precipitate
  3. filtrationwas collected by filtration
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-ca540a040e4345979095e68bbca15e30
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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