Triethyl phosphite → Diethyl 3-fluorobenzylphosphonate

HRID 928049Notes

Reaction equation

HRID 928049 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[P:10]([O:17]CC)([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13]>>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 680073-Fluorobenzyl bromide

Product 1

HCID 11311157Diethyl 3-fluorobenzylphosphonate

Conditions

Temperature
160 °C

Procedure

A mixture of 3-fluorobenzyl bromide (2 g) and triethyl phosphite (2.2 mL) was heated at 160° C. under nitrogen for 4 hours. After cooling, the were volatiles removed in vacuo and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100% to give diethyl (3-fluorobenzyl)phosphonate (2.46 g)

Workup

  1. temperatureAfter cooling
  2. customthe were volatiles removed in vacuo
  3. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100%

Sources & evidence

ORD record
ord-28b00569f5bf49409286c1aa20be08a0
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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