Trimethyl phosphite → 4-(Dimethoxyphosphorylmethylphenyl)cinnamonitrile

HRID 1979674Notes

Reaction equation

HRID 1979674 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([CH:7]=[CH:8][C:9]#[N:10])=[CH:5][CH:4]=1.[CH3:13][O:14][P:15]([O:18][CH3:19])[O:16]C>>[CH3:13][O:14][P:15]([CH2:6][C:5]1[CH:4]=[CH:3][CH:12]=[CH:11][C:2]=1[C:3]1[CH:12]=[CH:11][C:6]([CH:7]=[CH:8][C:9]#[N:10])=[CH:5][CH:4]=1)([O:18][CH3:19])=[O:16]

Participants

3

Reactant 2

HCID 8472Trimethyl phosphite2×HCID 540804474-Bromomethylcinnamonitrile

Product 1

HCID 544756744-(Dimethoxyphosphorylmethylphenyl)cinnamonitrile

Conditions

Temperature
0 °C

Procedure

390 g of 4-bromomethylcinnamonitrile are suspended in 600 ml of trimethylphosphite and the suspension is added in portions to 250 ml of well stirred trimethylphosphite of 90° C., such that the strongly exothermic reaction can be kept under control. Excess trimethylphosphite is then distilled off under a water jet vacuum and 330 ml of toluene and 660 ml of hexane are added to the residue, which is cooled to 0° C. The crystallised product is filtered with suction and vacuum dried at 50° C., affording 427 g of 4-(dimethoxyphosphorylmethylphenyl)cinnamonitrile with a melting point of 98°-101° C.

Workup

  1. distillationExcess trimethylphosphite is then distilled off under a water jet vacuum and 330 ml of toluene and 660 ml of hexane
  2. additionare added to the residue, which
  3. filtrationThe crystallised product is filtered with suction and vacuum
  4. customdried at 50° C.

Sources & evidence

ORD record
ord-416f4d86dc5f474db8b0cc5fdb94b26b
Source dataset
uspto-grants-1984_11
Patent number
US04482496

Reaction notes

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