Triethyl phosphite → Methyl 4-(diethoxyphosphorylmethyl)benzoate

HRID 1462385Notes

Reaction equation

HRID 1462385 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11]Br)=[CH:7][CH:6]=1)=[O:4].[P:13]([O:20]CC)([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16]>>[CH2:15]([O:14][P:13]([CH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1)([O:17][CH2:18][CH3:19])=[O:20])[CH3:16]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 10946061Methyl 4-(diethoxyphosphorylmethyl)benzoate

Procedure

A mixture of 2.29 g (10 mmol) of methyl 4-bromomethyl benzoate and 1.66 g (10 mmol) of freshly distilled triethyl phosphite was heated at 150°-160° C. for 3 hours. Any unreacted phosphite was purged in vacuo and the residual phosphonate ester was suitable for use in the next step; m/e 286; NMR (CDCl3) 1.25 (6H, t, OCH2CH3), 3.20 (2H, d, J=22 Hz, CH2P), 3.93 (3H, s, OCH3), 4.05 (4H, q, OCH2), 7.40 (2H, d, 3,5-H's), 8.05 (2H, d, 2,6-H's).

Workup

  1. temperaturewas heated at 150°-160° C. for 3 hours
  2. customAny unreacted phosphite was purged in vacuo

Sources & evidence

ORD record
ord-56b63c1908e24291872a03a358460cc6
Source dataset
uspto-grants-1984_07
Patent number
US04460591

Reaction notes

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