Hydrogen Bromide → 4-Chloro-2-fluorobenzyl bromide

HRID 368797Notes

Reaction equation

HRID 368797 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([F:9])[CH:3]=1.OS(O)(=O)=O.[BrH:15].N(C(C)(C)C#N)=NC(C)(C)C#N.OO>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:15])=[C:4]([F:9])[CH:3]=1

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 6547Azobisisobutyronitrile2×HCID 5206304-Chloro-2-fluorotoluene

Product 1

HCID 27365514-Chloro-2-fluorobenzyl bromide

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

361.5 g of 4-chloro-2-fluorotoluene, 520 g of chlorobenzene, 6 g of conc. H2SO4, 467 g of 47% strength hydrobromic acid and 2.7 g of 2,2'-azobis(2-methylpropionitrile) were mixed at 70° C. in a 4 l stirred apparatus. 620.5 g of a 10% strength aqueous hydrogen peroxide solution and a solution of 16.5 g of 2,2'-azobis(2-methylpropionitrile) in 270 g of chlorobenzene were simultaneously added dropwise over the course of 1.5 hours. The mixture was then stirred at 70° C. for 1 hour. GC analysis of the org. phase:

Workup

  1. stirringThe mixture was then stirred at 70° C. for 1 hour

Sources & evidence

ORD record
ord-53fa43640059453fb01ab66a7d352236
Source dataset
uspto-grants-2000_10
Patent number
US06133468

Reaction notes

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