Bromine → 4-(Bromoacetyl)benzonitrile

HRID 2248961Notes

Reaction equation

HRID 2248961 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-7f2d02c0ce3740e9bf2ae6cfbc7e07f1
Source dataset
uspto-grants-1991_08
Patent number
US05041567

Reaction notes

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