Triethyl phosphite → HCID 87832425, compound

HRID 970238Notes

Reaction equation

HRID 970238 reaction equation
[C:1]([C:3]1[C:8]([CH2:9]Br)=[C:7]([C:11]#[N:12])[C:6]([CH2:13]Br)=[C:5]([C:15]#[N:16])[C:4]=1[CH2:17]Br)#[N:2].[P:19]([O:26]CC)([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22]>C1(C)C=CC=CC=1>[C:1]([C:3]1[C:8]([CH2:9][P:19]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:26])=[C:7]([C:11]#[N:12])[C:6]([CH2:13][P:19]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:26])=[C:5]([C:15]#[N:16])[C:4]=1[CH2:17][P:19]([O:20][CH2:21][CH3:22])([O:23][CH2:24][CH3:25])=[O:26])#[N:2]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 713608692,4,6-Tris(bromomethyl)benzene-1,3,5-tricarbonitrile

Product 1

HCID 87832425HCID 87832425, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1,3,5-tricyano-2,4,6-tris(bromomethyl)benzene (1.0 g, 2.3 mmol) and P(OEt)3 (1.6 g, 14 mmol) in 60 mL of toluene was refluxed for 4 hrs. The solvent was removed in vacuo and the product was purified by column chromatography with hexane/ethyl acetate (10/1) as the eluent to obtain colorless oil. Yield, 0.97 g (69%); IR 2299 (CN), 1263 (P═O); 1H NMR δ 4.21 (q, 12H, J=7.2), 3.73 (d, 6H, J=22.1) 1.32 (t, 18H, J=7.2).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe product was purified by column chromatography with hexane/ethyl acetate (10/1) as the eluent
  3. customto obtain colorless oil
  4. customYield

Sources & evidence

ORD record
ord-eda941542b9e4ac1bb155456bd8fca42
Source dataset
uspto-grants-2007_12
Patent number
US07311860B2

Reaction notes

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