Trimethyl phosphite → 4-(Dimethoxy-phosphorylmethyl)-benzoic acid methyl ester

HRID 971060Notes

Reaction equation

HRID 971060 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]([O:18]C)([O:16][CH3:17])[O:14][CH3:15]>>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[CH:12][C:3]([CH2:2][P:13]([O:16][CH3:17])([O:14][CH3:15])=[O:18])=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 8472Trimethyl phosphiteHCID 256687Methyl 4-(bromomethyl)benzoate2×

Product 1

HCID 108011704-(Dimethoxy-phosphorylmethyl)-benzoic acid methyl ester

Procedure

Methyl 4-(bromomethyl)benzoate (compound 47) (11.2 g, 49 mmol) was dissolved in 25 mL trimethyl phosphite and refluxed under N2 for 5 hrs. Excess trimethyl phosphite was removed by co-distillation with toluene to give crude 4-(Dimethoxy-phosphorylmethyl)-benzoic acid methyl ester (compound 48).

Workup

  1. temperaturerefluxed under N2 for 5 hrs
  2. customExcess trimethyl phosphite was removed by co-distillation with toluene

Sources & evidence

ORD record
ord-034b96d633064f8bb315816c2ac56e38
Source dataset
uspto-grants-2007_12
Patent number
US07312336B2

Reaction notes

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