Bromine → 4-(Bromoacetyl)benzonitrile

HRID 1194052Notes

Reaction equation

HRID 1194052 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[Br:16]Br>CCOCC>[C:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1](=[O:3])[CH2:2][Br:16])=[CH:5][CH:6]=1)#[N:9]

Participants

5

Reactant 3

HCID 24408BromineHCID 740444'-CyanoacetophenoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 986544-(Bromoacetyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Acetylbenzonitrile (14.5 g, 100 mmol) was dissolved in anhydrous ether (150 ml). Aluminium chloride (catalytic amount) was added to the solution. Bromine (5.1 ml, 100 mmol) was added dropwise at room temperature and the solution stirred for 1/2 h. A precipitate formed and was collected and dried to yield p-cyanophenacyl bromide, m.p. 85°-86° C. (19.34 g, 86%); δH (CDCl3) 7.80 and 8.10 (4H, ABq, aryl), 4.45 (2H, s, CH2).

Workup

  1. customA precipitate formed
  2. customwas collected
  3. customdried

Sources & evidence

ORD record
ord-06c469dae602446e9d747ef56dde6b7e
Source dataset
uspto-grants-1989_03
Patent number
US04812470

Reaction notes

Loading…