N-bromobutanimide → 5-(Bromomethyl)-2-chlorobenzonitrile

HRID 1194716Notes

Reaction equation

HRID 1194716 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[C:4]#[N:5].[Br:11]N1C(=O)CCC1=O>C1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][Br:11])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 125572002-Chloro-5-methylbenzonitrile

Product 1

HCID 140330355-(Bromomethyl)-2-chlorobenzonitrileYield 30.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 2-chloro-5-methylbenzonitrile (10.6 g, 69.9 mmol), N-bromosuccinimide (12.2 g, 68.5 mmol), and dibenzoyl peroxide (349 mg, 1.44 mmol) in benzene (350 ml) was refluxed 1.5 hours, cooled, and evaporated to dryness under vacuum. The residue was suspended in 7:3 (v/v) hexane-dichloromethane, filtered, and evaporated. The crude product was chromatographed on silica gel (650 g) eluted with 7:3 (v/v) hexane-dichloromethane to provide 4.8 g (30%) 4-chloro-3-cyanobenzyl bromide, m.p. 55°-58° C.

Workup

  1. temperaturewas refluxed 1.5 hours
  2. temperaturecooled
  3. customevaporated to dryness under vacuum
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was chromatographed on silica gel (650 g)
  7. washeluted with 7:3 (v/v) hexane-dichloromethane

Sources & evidence

ORD record
ord-df76d66bf66e4a0f825f92a8343fa05c
Source dataset
uspto-grants-1989_03
Patent number
US04816469

Reaction notes

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