Bromine → HCID 15171714, compound

HRID 1681122Notes

Reaction equation

HRID 1681122 reaction equation
[Br:1]Br.[C:3]([C:6]1[CH:17]=[CH:16][C:9]2[C:10](=[O:15])[CH:11]=[C:12]([CH3:14])[O:13][C:8]=2[CH:7]=1)(=[O:5])[CH3:4].C(Cl)Cl.CO>C(O)(=O)C>[C:3]([C:6]1[CH:17]=[CH:16][C:9]2[C:10](=[O:15])[C:11]([Br:1])=[C:12]([CH3:14])[O:13][C:8]=2[CH:7]=1)(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 24408BromineHCID 15171713HCID 15171713, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 15171714HCID 15171714, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

77.5 ml of a 10% solution of bromine in acetic acid are added at 60° C., under an inert atmosphere, to a solution of 8.8 g (40.10-3 mol) of 7-acetyl-2-methyl-4H-1-benzopyran-4-one in 80 ml of acetic acid. The reaction mixture is kept at 60° C. for 2 hours and is then left to stand for 12 hours. It is concentrated under reduced pressure and the residue is then neutralized with a saturated solution of sodium bicarbonate. After extraction with ethyl acetate, the organic phase is washed with water until the pH of the washings is neutral, dried over magnesium sulfate and concentrated to dryness. After chromatography on silica gel using a methylene chloride/methanol mixture (12/1 v/v) as the eluent, 2.3 g (yield: 19%) of the expected product are obtained.

Workup

  1. waitis then left
  2. waitto stand for 12 hours
  3. concentrationIt is concentrated under reduced pressure
  4. extractionAfter extraction with ethyl acetate
  5. washthe organic phase is washed with water until the pH of the washings
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-49e5c0f0625d43cca91bccf57bf894cc
Source dataset
uspto-grants-1992_12
Patent number
US05169838

Reaction notes

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