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

HRID 1742330Notes

Reaction equation

HRID 1742330 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-04b3b6fbdbcd4079821fa6a1be71893f
Source dataset
uspto-grants-1994_08
Patent number
US05338734

Reaction notes

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