Triethyl phosphite → (5-Chloro-2-fluoro-benzyl)-phosphonic acid diethyl ester

HRID 2354116Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH2:7]Br.[CH2:11]([O:13][P:14]([O:18]CC)[O:15][CH2:16][CH3:17])[CH3:12]>C1COCC1>[CH2:11]([O:13][P:14]([CH2:7][C:6]1[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[F:10])(=[O:18])[O:15][CH2:16][CH3:17])[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

5-Chloro-2-fluoro-benzylbromide (630 g, purity according to GC 72% a/a, 2.42 mol) was heated at 100° C. and triethylphosphite (403 g, 2.42 mol) was added slowly in 1 h 45. The mixture was stirred for 2 hours at 100° C., and slowly THF (350 ml) was added and distilled off, until no ethylbromide was detected by NMR. To isolate the crude (5-chloro-2-fluoro-benzyl)-phosphonic acid diethyl ester the reaction mixture was cooled to room temperature, yielding 681 grams (100%).

Workup

distillationdistilled off, until no ethylbromide

Sources & evidence

ORD record: ord-e6e0902f1b5e44cba08afe93ee89bbac
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750167B2

Reaction notes

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