N-bromobutanimide → 2-Bromo-1-(bromomethyl)-4-fluorobenzene

HRID 231446Notes

Reaction equation

HRID 231446 reaction equation
[Br: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>[Br: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 740162-Bromo-4-fluorotoluene

Product 1

HCID 107069772-Bromo-1-(bromomethyl)-4-fluorobenzeneYield 100.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

By the method of Example 7, Step C, 75 g (0.40 mole) of 2-bromo-4-fluorotoluene, 70.6 g (0.40 mole) of N-bromosuccinimide, and 2.5 g (0.03 mole) of benzoyl peroxide were reacted in 450 ml of carbon tetrachloride, yielding 107.8 g of impure 2-bromo-4-fluorobenzyl bromide (68% assay).

Sources & evidence

ORD record
ord-cd61df16fa9a4f7da91b0735c126bb45
Source dataset
uspto-grants-1989_07
Patent number
US04846882

Reaction notes

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