N-bromobutanimide → 1-(Bromomethyl)-2-chloro-4-fluorobenzene

HRID 231440Notes

Reaction equation

HRID 231440 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][Br:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 967472-Chloro-4-fluorotoluene

Product 1

HCID 27250621-(Bromomethyl)-2-chloro-4-fluorobenzeneYield 75.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

By the method of Example 7, Step C, 141.4 g (0.978 mole) of 2-chloro-4-fluorotoluene, 175.8 g (0.978 mole) of N-bromosuccinimide, and 5.0 g of benzoyl peroxide in 15 liters of carbon tetrachloride were reacted, yielding 165 g of 2-chloro-4-fluorobenzyl bromide as a white solid.

Sources & evidence

ORD record
ord-92bbe4b3fa884de7adea63d2004552e8
Source dataset
uspto-grants-1989_07
Patent number
US04846882

Reaction notes

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