N-bromobutanimide → 3-(Bromomethyl)-5-methylbenzonitrile

HRID 426290

Reaction equation

HRID 426290 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:10])[CH:9]=1)[C:5]#[N:6].[Br:11]N1C(=O)CCC1=O>[W].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:10])[CH:9]=1)[C:5]#[N:6]

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 897183,5-Dimethylbenzonitrile

Product 1

HCID 145678603-(Bromomethyl)-5-methylbenzonitrileYield 81.3%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of carbon tetrachloride (270 mL), was added 3,5-dimethylbenzonitrile (37 g, 0.282M), N-bromo succinimide (NBS) (50 g, 0.282 M), and benzoyl peroxide (3.4 g, 14 mmol). The mixture was then refluxed for 3 hr. under a light of 500 W tungsten lamp. After cooling to room temperature, the mixture was filtered, evaporated, and the residue was purified by silica gel column chromatography (eluent, ether:hexane (1:10)) to give 48 g (81%) of 3-(bromomethyl)-5-methylbenzonitrile as a white solid. m.p. 80-81° C. 1H NMR (200 MHz, CDCl3) δ 2.39 (3H, s), 4.43 (2H, s), 7.39 (1H, s), 7.43 (1H, s), 7.48 (1H, s).

Workup

  1. temperatureThe mixture was then refluxed for 3 hr
  2. filtrationthe mixture was filtered
  3. customevaporated
  4. customthe residue was purified by silica gel column chromatography (eluent, ether:hexane (1:10))

Sources & evidence

ORD record
ord-008517b05fe14f49bc88e83587e6bb8c
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Linked notes

Loading…