2,6-Lutidine → 3,5-Dibromosalicyl 3-butenoate

HRID 567667

Reaction equation

HRID 567667 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH:3]=[CH2:4].[Br:7][C:8]1[CH:16]=[C:15]([Br:17])[CH:14]=[C:10]([C:11]([OH:13])=O)[C:9]=1[OH:18].N1C(C)=CC=CC=1C>CC(C)=O>[C:1]([O:13][CH2:11][C:10]1[C:9](=[C:8]([Br:7])[CH:16]=[C:15]([Br:17])[CH:14]=1)[OH:18])(=[O:5])[CH2:2][CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 184643,5-Dibromosalicylic acidHCID 10975427But-3-enoyl Chloride

Product 1

HCID 212622063,5-Dibromosalicyl 3-butenoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3,5-Dibromosalicyl 3-butenoate is prepared by reaction of an acetone solution of 3-butenoyl chloride and 3,5-dibromosalicylic acid in the presence of 2,6-lutidine. The 3-butenoate ester is isolated and purified. In a second step, the desired oxirane, 3,5-dibromosalicyl 3,4-oxabutanoate, is prepared by reaction of 3,5-dibromosalicyl 3-butenoate and 3-chloroperbenzoic acid in chloroform solution. The desired oxirane is isolated and purified.

Sources & evidence

ORD record
ord-137ef8ba307b4b909a8d6201c4b20be9
Source dataset
uspto-grants-2001_01
Patent number
US06180598B2

Linked notes

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