Triethyl phosphite → Phosphonic acid, [(3-cyanophenyl)methyl]-, diethyl ester

HRID 343575

Reaction equation

[P:1]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])[O:2]CC.[C:11]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16]Br)#[N:12]>>[CH2:9]([O:8][P:1]([CH2:16][C:15]1[CH:18]=[CH:19][CH:20]=[C:13]([C:11]#[N:12])[CH:14]=1)(=[O:2])[O:5][CH2:6][CH3:7])[CH3:10]

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 21466817Phosphonic acid, [(3-cyanophenyl)methyl]-, diethyl esterYield 84%

Conditions

Temperature: 140 °C

Procedure

A stirrd mixture of triethyl phosphite (0.500 g, 2.95 mmol) and 3-cyanobenzyl bromide (0.609 g, 2.95 mmol) was refluxed at 140° C. under argon for 2 h and the resulting volatiles were removed at room temperature in vacuo to afford the tided intermediate as a colorless oil (0.62 g, 84%). 1H-NMR (400 MHz, CDCl3) δ 7.7-7.5 (m, 3H), 7.44 (t, J=7.8 Hz, 1H), 4.06 (p, J=7.6 Hz, 4H), 3.17 (d J=21.8 Hz, 2H), 1.27 (t, J=7.1 Hz, 6H).

Workup

customthe resulting volatiles were removed at room temperature in vacuo

Sources & evidence

ORD record: ord-fabcae08b6df40c082c16e89c9736d44
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05861421

Linked notes

Loading…