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

HRID 911598Notes

Reaction equation

HRID 911598 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([Cl:17])[CH:11]=1>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])=[C:12]([Cl:17])[CH:11]=1

Participants

5

Reactant 2

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

Product 1

HCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzeneYield 61%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

Add NBS (13.171 g, 74 mmol) and benzoyl peroxide (152 mg, 0.63 mmol) to a solution of 4-bromo-2-chlorotoluene (15.2 g, 74 mmol) in carbon tetrachloride (152 mL) and stir for 6 days at 90° C. Cool to 0° C., filter the mixture and concentrate the filtrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (99:1) to obtain the desired intermediate as a yellow oil (12.7 g, 61%).

Workup

  1. temperatureCool to 0° C.
  2. filtrationfilter the mixture
  3. concentrationconcentrate the filtrate in vacuo
  4. customPurify by chromatography on silica gel eluting with hexane/EtOAc (99:1)

Sources & evidence

ORD record
ord-aadfa04a5ef54f78af904064efd0c380
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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