3-(4-Methylphenyl)prop-2-enenitrile → 4-Bromomethylcinnamonitrile

HRID 1902882Notes

Reaction equation

HRID 1902882 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][C:8]#[N:9])=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][C:8]#[N:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 342423-(4-Methylphenyl)prop-2-enenitrileHCID 67184N-bromobutanimide

Product 1

HCID 540804474-Bromomethylcinnamonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

88 g of 4-bromomethylcinnamonitrile (obtained by bromination of 4-methylcinnamonitrile with N-bromosuccinimide in carbon tetrachloride, and having a melting point of 105°-107° C.) are mixed with 256 g of triethylphosphite. The mixture is then slowly heated to 150° C. with stirring, and then stirred for 3 hours at this temperature. Excess phosphite is then removed in vacuo, affording the crude phosphonate of the formula ##STR68## in the form of a light brown oil.

Sources & evidence

ORD record
ord-5f13d88c67494bdf84c0566407e9e67d
Source dataset
uspto-grants-1982_12
Patent number
US04366189

Reaction notes

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