Nitrogen → Diethyl 3-trifluoromethylbenzylphosphonate

HRID 1720851Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Cl.[P:13]([O:20]CC)([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16].N#N>>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH2:6][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])[CH:8]=[CH:9][CH:10]=1

Participants

Reactant 3

HCID 947Nitrogen

HCID 31215Triethyl phosphite

HCID 697163-(Trifluoromethyl)benzyl chloride

Product 1

HCID 11162251Diethyl 3-trifluoromethylbenzylphosphonate

Conditions

Temperature: 160 °C

Procedure

3-Trifiuoromethylbenzylchloride (50 g, 257 mmol) and triethyl phosphite (53.4 g, 321 mmol) were combined,under N2, and heated to 160° C. for 18 hours. The reaction mixture was distillated at 105°-110° C. to give 69.5 g (91.3%) of analytically pure product as a colorless oil. 300 MHz 1H NMR (CDCl3): δ, 3.20 (d,2H, J=21.78 Hz, PCH2). MS: 297 (M+1).

Workup

customwas distillated at 105°-110° C.
customto give 69.5 g (91.3%) of analytically pure product as a colorless oil

Sources & evidence

ORD record: ord-8afd5ee61c8945cdb9871eeec1c6d71e
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05508273

Reaction notes

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