Benzoyl Peroxide → 3-(Bromomethyl)-1,2,4,5-tetrafluorobenzene

HRID 1164548

Reaction equation

HRID 1164548 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[C:3]=1[CH3:11].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[C:3]=1[CH2:11][Br:12]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 788962,3,5,6-Tetrafluorotoluene

Product 1

HCID 1043773-(Bromomethyl)-1,2,4,5-tetrafluorobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2,3,5,6-tetrafluorotoluene (1.7 g), N-bromosuccinimide (1.9 g), dry carbon tetrachloride (10 ml) and benzoyl peroxide (0.01 g) was heated at the reflux temperature for 20 hours, cooled to the ambient temperature (ca.25° C.) filtered and the filtrate diluted with diethyl ether. The ethereal solution was washed with water, dried over anhydrous magnesium sulphate and concentrated by evaporation of the solvents to yield 2,3,5,6-tetrafluorobenzyl bromide as a mobile colourless oil.

Workup

  1. temperaturewas heated at the reflux temperature for 20 hours
  2. filtrationfiltered
  3. additionthe filtrate diluted with diethyl ether
  4. washThe ethereal solution was washed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated by evaporation of the solvents

Sources & evidence

ORD record
ord-8fc3a240a9194d0dba4b7b2cf1fd0e24
Source dataset
uspto-grants-1983_01
Patent number
US04370346

Linked notes

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