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

HRID 635231Notes

Reaction equation

HRID 635231 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:18]C)([O:16][CH3:17])[O:14][CH3:15]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][P:13]([O:16][CH3:17])([O:14][CH3:15])=[O:18])=[CH:7][CH:6]=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-3d483c3b74624bc3b5db8015348cd15f
Source dataset
uspto-grants-2001_02
Patent number
US06187792B1

Reaction notes

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