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

HRID 911595Notes

Reaction equation

HRID 911595 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[Cl:17]>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][Br:8])=[CH:12][C:11]=1[Cl:17]

Participants

5

Reactant 2

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

Product 1

HCID 129473921-Bromo-4-(bromomethyl)-2-chlorobenzeneYield 85.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

Add NBS (5.266 g, 23.9 mmol) and benzoyl peroxide (49 mg, 0.2 mmol) to a solution of 4-bromo-3-chlorotoluene (4.925 g, 23.9 mmol) in carbon tetrachloride (49 mL) and heat overnight at 90° C. Cool to 0° C. and filter the mixture. Concentrate the filtrate in vacuo to obtain the desired intermediate as a yellow oil (5.807 g, 85%).

Workup

  1. temperatureCool to 0° C.
  2. filtrationfilter the mixture
  3. concentrationConcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-a3a893bd5e9c4ab48735f2fb1be93928
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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