Allyl bromide → HCID 19425362, compound

HRID 742193Notes

Reaction equation

HRID 742193 reaction equation
[Cl:1][C:2]1[C:10]([OH:11])=[C:9]([OH:12])[C:8]([Cl:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[CH:21]=[CH2:22]>CN(C=O)C>[Cl:1][C:2]1[C:10]([O:11][CH2:10][CH:2]=[CH2:3])=[C:9]([O:12][CH2:9][CH:8]=[CH2:7])[C:8]([Cl:13])=[CH:7][C:3]=1[C:4]([O:6][CH2:20][CH:21]=[CH2:22])=[O:5]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 50914Benzoic acid, dichloro-3,4-dihydroxy-

Product 1

HCID 19425362HCID 19425362, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,5-Dichloro-3,4-dihydroxybenzoic acid (10.7 g, see J. Antibiotics, 1987, 40, 22) and K2CO3 (33.1 g) were suspended in DMF (150 ml), and treated with allyl bromide (14.7 ml). After stirring overnight, the mixture was filtered, diluted with ethyl acetate, washed with sodium bicarbonate, dried (MgSO4), filtered and evaporated to give allyl 2,5-dichloro-3,4-diallyloxybenzoate (14.7 g): NMR (CDCl3) 4.55-4.65 (m, 4H); 4.82 (m, 2H); 5.24-5.50 (m, 6H); 5.94-6.22 (m, 3H); 7.70 (s, 1H).

Workup

  1. filtrationthe mixture was filtered
  2. additiondiluted with ethyl acetate
  3. washwashed with sodium bicarbonate
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-08d446f2e4c044c69a0587c7c4197137
Source dataset
uspto-grants-1996_09
Patent number
US05554606

Reaction notes

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