4-Bromotoluene → p-Tolunitrile

HRID 2233279Notes

Reaction equation

HRID 2233279 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Cu]([C:12]#[N:13])C#N>CN(C)C=O>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]#[N:13])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 78054-BromotolueneHCID 178418260HCID 178418260, compound

Product 1

HCID 7724p-Tolunitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bromo-4-methyl-benzene of general formula H-1, where B, R1, R2, R3 and R4 are as defined above is reacted with copper cyanide in a polar solvent as dimethylformamide at elevated temperature to obtain the 4-methyl-benzonitrile of general formula H-2. The 4-methyl-benzonitrile of general formula H-2 is brominated by the treatment with N-bromosuccinimide in refluxing tetrachloromethane in the presence of a radical initiator like AIBN to obtain the 4-Bromomethyl-benzonitrile of general formula H-3.

Sources & evidence

ORD record
ord-e491a30554314a10886cb79db4d323bf
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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