N-bromobutanimide → 1-Bromo-4-(bromomethyl)-2-chlorobenzene

HRID 2052537Notes

Reaction equation

HRID 2052537 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[Cl:9].[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:10])=[CH:4][C:3]=1[Cl:9]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1387894-Bromo-3-chlorotoluene

Product 1

HCID 129473921-Bromo-4-(bromomethyl)-2-chlorobenzeneYield 100.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

4-bromo-3-chlorotoluene [31.8 g, described by Cohen and Raper, J. Chem. Soc., 85, 1267 (1904)] was heated with N-bromosuccinimide (27.5 g) and benzoyl peroxide (3.6 g) in carbon tetrachloride (75 ml) at reflux for 10 hours. The cooled solution was filtered, washed with aqueous ferrous sulphate solution, dried over magnesium sulphate, filtered and evaporated to dryness. 4-Bromo-3-chlorobenzyl bromide (44 g) was obtained as a pale orange oil.

Workup

  1. temperatureat reflux for 10 hours
  2. filtrationThe cooled solution was filtered
  3. washwashed with aqueous ferrous sulphate solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-cff0d882cd234760945171b90bc88e27
Source dataset
uspto-grants-1980_01
Patent number
US04185992

Reaction notes

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