Benzoyl Peroxide → 1-(Bromomethyl)-4-chloro-2-methoxybenzene

HRID 543909Notes

Reaction equation

HRID 543909 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[Br:11]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:11])=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2928585-CHLORO-2-METHYLANISOLE

Product 1

HCID 223274741-(Bromomethyl)-4-chloro-2-methoxybenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Bromination of 4-chloro-2-methoxytoluene by means of N-bromosuccinimide in boiling carbon tetrachloride in the presence of dibenzoyl peroxide produces 4-chloro-2-methoxybenzyl bromide as a colourless liquid which has a boiling point of 140°-145° C./13 mm Hg. Reaction of this compound with triethyl phosphite in boiling xylene turns it into diethyl 4-chloro-2-methoxybenzylphosphonate; this is a colourless, viscous liquid which has a boiling point of 132° C./0.1 mm Hg.

Sources & evidence

ORD record
ord-08044b080c1446d8b39801d26c827027
Source dataset
uspto-grants-1984_05
Patent number
US04447651

Reaction notes

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