Allyl bromide → HCID 21857121, compound

HRID 1383426Notes

Reaction equation

HRID 1383426 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[F:5][C:6]1[C:7](=[O:19])[O:8][C:9]2[C:14]([C:15]=1[CH3:16])=[CH:13][CH:12]=[C:11]([OH:17])[C:10]=2[CH3:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:5][C:6]1[C:7](=[O:19])[O:8][C:9]2[C:14]([C:15]=1[CH3:16])=[CH:13][CH:12]=[C:11]([O:17][CH2:3][CH:2]=[CH2:1])[C:10]=2[CH3:18]

Participants

5

Reactant 3

HCID 7841Allyl bromide2×HCID 11430Potassium CarbonateHCID 10798396HCID 10798396, compound

Product 1

HCID 21857121HCID 21857121, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Allyl bromide (1.08 mL, 12.48 mmoles) was added to a mixture of 3-fluoro-4,8-dimethyl-7-hydroxycoumarin (1.73 g, 8.31 mmoles), ca. 5 g of potassium carbonate and 45 mL of dry acetone. The reaction mixture was stirred under an inert atmosphere at room temperature for 28 hours. During this time, excess allyl bromide (1.44 mL, 16.64 mmoles) was added in two portions. The carbonate salt was removed by suction filtration washed with acetone and the solvent evaporated under reduced pressure yielding a solid, which was purified by recrystallisation from a mixture of methanol:water. Thus, 1.60 g (78% yield) of 3-fluoro-4,8-dimethyl-7-allyloxycoumarin was obtained as a white solid: mp 117° C.

Workup

  1. customThe carbonate salt was removed by suction filtration
  2. washwashed with acetone
  3. customthe solvent evaporated under reduced pressure
  4. customyielding a solid, which
  5. customwas purified by recrystallisation from a mixture of methanol

Sources & evidence

ORD record
ord-2916b82184b5426d95cf375df2ee0c68
Source dataset
uspto-grants-2001_07
Patent number
US06255324B1

Reaction notes

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