N-bromobutanimide → 1-(Bromomethyl)-4-fluoro-2-iodobenzene

HRID 1389281Notes

Reaction equation

HRID 1389281 reaction equation
[I: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>ClC(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[F:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:9][Br:10])=[C:2]([I:1])[CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 832204-Fluoro-2-iodotoluene

Product 1

HCID 128060541-(Bromomethyl)-4-fluoro-2-iodobenzeneYield 78.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 23.6 g of 2-iodo-4-fluorotoluene in 50 ml of tetrachloromethane was treated with 0.2 g of dibenzoyl peroxide and 19.6 g of N-bromosuccinimide. The mixture was then refluxed for 6 hours and illuminated by a 200 W bulb. After cooling, the spearated succinimide was filtered off and washed with 15 ml tetrachloromethane. The filtrate was evaporated and the residue distilled. There was obtained 24.8 g of 4-fluoro-2-iodobenzyl bromide with a b.p. of 130°-140° C./20 Torr. The product crystallized on standing and a sample recrystallized from petroleum ether; m.p. 71°-73° C.

Workup

  1. temperatureThe mixture was then refluxed for 6 hours
  2. customilluminated by a 200 W bulb
  3. temperatureAfter cooling
  4. filtrationthe spearated succinimide was filtered off
  5. washwashed with 15 ml tetrachloromethane
  6. customThe filtrate was evaporated
  7. distillationthe residue distilled

Sources & evidence

ORD record
ord-99b55139ae424b89920124c3fc5871d6
Source dataset
uspto-grants-1981_01
Patent number
US04243805

Reaction notes

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