Benzoyl Peroxide → 4-(Bromomethyl)benzoic acid

HRID 867030Notes

Reaction equation

HRID 867030 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][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

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

Product 1

HCID 225994-(Bromomethyl)benzoic 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 α-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. In slightly higher temperatures, above -10° C, the corresponding dinitro derivative 4a predominates.

Sources & evidence

ORD record
ord-0a88b6393b524af68346989d2cbeb68b
Source dataset
uspto-grants-1978_07
Patent number
US04101721

Reaction notes

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