Benzoyl Peroxide → AGN-PC-0NH77L

HRID 2055034Notes

Reaction equation

HRID 2055034 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([O:27][C:28](=[O:30])[CH3:29])[CH:8]=[CH:9][C:10]=1[C:11]1[C:12](=[O:26])[O:13][C:14]2[C:19]([C:20]=1[CH3:21])=[CH:18][CH:17]=[C:16]([O:22][C:23](=[O:25])[CH3:24])[CH:15]=2)(=[O:3])[CH3:2].[Br:31]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.[W]>[C:1]([O:4][C:5]1[CH:6]=[C:7]([O:27][C:28](=[O:30])[CH3:29])[CH:8]=[CH:9][C:10]=1[C:11]1[C:12](=[O:26])[O:13][C:14]2[C:19]([C:20]=1[CH2:21][Br:31])=[CH:18][CH:17]=[C:16]([O:22][C:23](=[O:25])[CH3:24])[CH:15]=2)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 7187Benzoyl Peroxide2×HCID 67184N-bromobutanimide2×HCID 11200702[3-(2,4-diacetyloxyphenyl)-4-methyl-2-oxochromen-7-yl] acetate

Product 1

HCID 11179317AGN-PC-0NH77L

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of acetic acid 3-acetoxy-4-(7-acetoxy-4-methyl-2-oxo-2H-chromen-3-yl)phenyl ester (0.767 g, 1.87 mmol, 1 eq), N-bromosuccinimide (0.349 g, 1.962 mmol, 1.05 eq) and benzoyl peroxide (0.035 g, 0.145 mmol) in carbon tetrachloride (30 mL) was stirred and heated to reflux under nitrogen in presence of a 100 W tungsten lamp for 20 hours. Reaction monitoring by MS and TLC showed the presence unreacted starting material, and additional N-bromosuccinimide (0.060 g, 0.34 mmol) and benzoyl peroxide (0.008 g) were added to the reaction mixture and the reaction was heated at reflux under nitrogen for an additional 2 hours. The mixture was evaporated to dryness, dissolved in hot dichloromethane and purified by column chromatography on silica gel using 3% ethyl acetate/hexane as an eluent to yield the title product as a tan crystalline solid.

Workup

  1. temperatureheated
  2. customReaction monitoring by MS and TLC
  3. additionwere added to the reaction mixture
  4. temperaturethe reaction was heated
  5. temperatureat reflux under nitrogen for an additional 2 hours
  6. customThe mixture was evaporated to dryness
  7. dissolutiondissolved in hot dichloromethane
  8. custompurified by column chromatography on silica gel using 3% ethyl acetate/hexane as an eluent

Sources & evidence

ORD record
ord-1d7353cc62844920a890facb0a42a295
Source dataset
uspto-grants-2008_02
Patent number
US07329654B2

Reaction notes

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