Benzoyl Peroxide → 3-Bromo-4-methylbenzoic acid

HRID 1449248Notes

Reaction equation

HRID 1449248 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[CH:6][CH:7]=1.[Br:11]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1>[Br:11][C:7]1[CH:6]=[C:5]([C:8]([OH:10])=[O:9])[CH:4]=[CH:3][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 7470P-Toluic AcidHCID 67184N-bromobutanimide

Product 1

HCID 821303-Bromo-4-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Briefly described, p-toluic acid 2 is refluxed with N-bromo-succinimide and benzoyl peroxide in dry benzene to give a bromo-p-toluic acid 3 which, upon reaction with nitric acid, is converted to 3-nitro-4-bromomethyl benzoic acid 4. This is believed to be a new compound and represents a parent compound in the synthesis forming the subject matter of this invention. At slightly higher temperatures, above -10° C., the corresponding dinitro derivative 4a predominates.

Sources & evidence

ORD record
ord-b3d130a825f44ee5b7586cd9c2e21cf2
Source dataset
uspto-grants-1980_02
Patent number
US04189605

Reaction notes

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