Bromide ion → Perbenzoic acid

HRID 1722487Notes

Reaction equation

HRID 1722487 reaction equation
[C:1]1([Se]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-].C1(S(Cl)=O)C=CC=CC=1.[OH:19][OH:20].C[CH2:22][O:23]CC>C(Cl)Cl>[C:22]([O:19][OH:20])(=[O:23])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 259Bromide ionHCID 784Hydrogen PeroxideHCID 3283Diethyl EtherHCID 21928Chloroselenobenzene2×HCID 4190003Benzenesulfinyl chloride

Product 1

HCID 523077Perbenzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The diene (2) of step (A) is treated with a halogenating agent such as phenylselenyl chloride or bromide or phenylsulfinyl chloride, preferably phenylselenyl chloride, in an approximately equimolar ratio in an inert solvent at about -80° C., for approximately 20 minutes; illustrative of such inert solvents are methylene chloride, ether and the like. After a standard workup the product residue is dissolved in an ethereal solvent, chilled to about 0° C. and oxidized with an agent such as 30% hydrogen peroxide or a peroxy acid such as peroxybenzoic acid to yield a halohydrin analog (3).

Workup

  1. dissolutionAfter a standard workup the product residue is dissolved in an ethereal solvent

Sources & evidence

ORD record
ord-af175490a8bf4daeb9844a21c9f6e8ac
Source dataset
uspto-grants-1989_08
Patent number
US04855456

Reaction notes

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