p-Fluorotoluene → 4-Fluorobenzyl bromide

HRID 434539

Reaction equation

HRID 434539 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.C1C(=O)N([Br:16])C(=O)C1>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:16])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 9603p-FluorotolueneHCID 67184N-bromobutanimide

Product 1

HCID 680214-Fluorobenzyl bromideYield 101.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A 300-ml flask was charged with 16.6 g of 4-fluorotoluene, 30.0 g of NBS, 0.5 g of benzoyl peroxide and 150 ml of carbon tetrachloride, and the mixture was refluxed for 2.0 hours. The reaction mixture was cooled to room temperature, and the formed precipitate was removed by filtration and the residual CCl4 solution was washed with dilute alkali and then with water, dried over Na2SO4, and evaporated under reduced pressure to give 28.8 g of crude 4-fluorobenzyl bromide.

Workup

  1. temperaturethe mixture was refluxed for 2.0 hours
  2. customthe formed precipitate was removed by filtration
  3. washthe residual CCl4 solution was washed with dilute alkali
  4. dry with materialwith water, dried over Na2SO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-488f31c16d854192accd904c27116779
Source dataset
uspto-grants-1983_08
Patent number
US04397864

Linked notes

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