N-bromobutanimide → 4-(Bromomethyl)-3-methoxybenzonitrile

HRID 1723230Notes

Reaction equation

HRID 1723230 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:14]#[N:15]>C(Cl)(Cl)(Cl)Cl.CCOCC.[W].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][CH2:19][C:18]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][C:11]=1[O:10][CH3:9]

Participants

7

Reactant 2

HCID 67184N-bromobutanimideHCID 147529943-Methoxy-4-methylbenzonitrile

Product 1

HCID 147529954-(Bromomethyl)-3-methoxybenzonitrileYield 65%

Reagents, catalysts & solvents 4

HCID 7187Benzoyl PeroxideCatalystHCID 23964TungstenCatalystHCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (3.2 g.) and benzoyl peroxide (0.005 g.) were added to a solution of 3-methoxy-4-methylbenzonitrile (2.65 g.) in dry carbon tetrachloride (90 ml.). The mixture was heated to reflux for 15 minutes using a 250 watt tungsten lamp. The cooled reaction mixture was diluted with petrolum ether (b.p. 60°-80° C., 90 ml.), insoluble material removed by filtration, and the filtrate evaporated. The solid residue was recrystallized from a mixture of dichloromethane and petroleum ether to give 4-bromomethyl-3-methoxybenzonitrile (W) (2.64 g., 65%) as a white solid, m.p. 87°-91° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 15 minutes
  3. customThe cooled reaction mixture
  4. customremoved by filtration
  5. customthe filtrate evaporated
  6. customThe solid residue was recrystallized from a mixture of dichloromethane and petroleum ether

Sources & evidence

ORD record
ord-bfdb42c0ba0e4c00881e54d1a729031d
Source dataset
uspto-grants-1989_08
Patent number
US04859692

Reaction notes

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