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

HRID 1245837Notes

Reaction equation

HRID 1245837 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([Cl:9])[CH:3]=1.[Br:10]N1C(=O)CCC1=O>ClC1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:10])=[C:4]([Cl:9])[CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27355544-Bromo-2-chlorotoluene

Product 1

HCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzeneYield 27.3%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

4-Bromo-2-chlorotoluene (7.02 g) and N-bromosuccinimide (6.07 g) was stirred in chlorobenzene (50 ml) under ultraviolet light at 100° C. for 18 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by medium-pressure liquid chromatography, eluting with iso-hexane, to give a colourless oil (2.65 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by medium-pressure liquid chromatography
  4. washeluting with iso-hexane

Sources & evidence

ORD record
ord-a356534d03544b708d2216ccac335ee9
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

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