Triethyl Phosphate → Methyl 4-(diethoxyphosphorylmethyl)benzoate

HRID 1394342Notes

Reaction equation

HRID 1394342 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[P:13](OCC)([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])=[O:14]>>[CH3:10][O:9][C:7]([C:6]1[CH:11]=[CH:12][C:3]([CH2:2][P:13](=[O:14])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])=[CH:4][CH:5]=1)=[O:8]

Participants

3

Reactant 2

HCID 6535Triethyl PhosphateHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 10946061Methyl 4-(diethoxyphosphorylmethyl)benzoateYield 69%

Conditions

Temperature
150 °C

Procedure

A mixture of methyl 4-(bromomethyl)benzoate (25 g, 109 mmol) and triethyl phosphate (24.3 ml, 142 mmol) was stirred at 150° C. for 24 h. The resulting mixture was purified by distillation (165-172° C., 1 mmHg) to obtain diethyl 4-(methoxycarbonyl)benzylphosphonate (21.5 g, 69%).

Workup

  1. distillationThe resulting mixture was purified by distillation (165-172° C., 1 mmHg)

Sources & evidence

ORD record
ord-19a843b9351d436baf54a536facbb37d
Source dataset
uspto-grants-2008_03
Patent number
US07348324B2

Reaction notes

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