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

HRID 1607928
Notes
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Reaction equation

HRID 1607928 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 colourlessoil.

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-1e894d1a67874e6783eab0da040c1559
Source dataset
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04868209

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes