4-Bromo-2-chlorotoluene → 4-Bromo-1-(bromomethyl)-2-chlorobenzene

HRID 1672735Notes

Reaction equation

HRID 1672735 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([Cl:9])[CH:3]=1.[Br:10]NC(=O)CCC(N)=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])=[C:4]([Cl:9])[CH:3]=1

Participants

5

Reactant 2

HCID 27355544-Bromo-2-chlorotolueneHCID 9834204N-Bromosuccinamide

Product 1

HCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzeneYield 71%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Dissolve 4-bromo-2-chloro-1-methyl-benzene (64.3 g, 312.9 mmol) in carbon tetrachloride (1 L). Add benzoyl peroxide (760 mg, 3.1 mmol) and N-bromosuccinamide (58.5 g, 329 mmol) and heat to 80° C. for 18 hours. Cool reaction to room temperature and filter. Concentrate the filtrate and purify by silica gel (hexanes) to yield 63 g (71%) of the title compound. NMR (CDCl3) δ 7.57 (d, 1H), 7.39 (dd, 1H), 7.31 (d, 1H), 4.53 (s, 2H).

Workup

  1. temperatureCool
  2. customreaction to room temperature
  3. filtrationfilter
  4. concentrationConcentrate the filtrate
  5. custompurify by silica gel (hexanes)

Sources & evidence

ORD record
ord-a0038c68bcc9430d9c7d9e17ca90450f
Source dataset
uspto-grants-2011_08
Patent number
US07998999B2

Reaction notes

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