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

HRID 1732774Notes

Reaction equation

HRID 1732774 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(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.ClC(Cl)(Cl)Cl>[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%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-bromo-4-fluorotoluene (37.4 g), N-bromosuccinimide (39 g), tetrachloromethane (120 ml) and benzoyl peroxide (0.25 g) is refluxed for 5 hours. After standing overnight, the separated succinimide is filtered off and the filtrate is taken down under diminished pressure, yielding 52 g (100%) of crude 2-bromo-4-fluorobenzyl bromide which can be used in the next step without purification. In order to characterize the pure compound, a sample can be distilled; b.p. 127° C./20 Torr.

Workup

  1. temperatureis refluxed for 5 hours
  2. filtrationthe separated succinimide is filtered off

Sources & evidence

ORD record
ord-c8c244e30f924820a47bbeead41319d9
Source dataset
uspto-grants-1980_12
Patent number
US04238611

Reaction notes

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