Trimethyl phosphite → (4-chlorobenzyl)-phosphonic acid dimethyl ester

HRID 1793645Notes

Reaction equation

HRID 1793645 reaction equation
[CH3:1][O:2][P:3]([O:6]C)[O:4][CH3:5].[Cl:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Br)=[CH:11][CH:10]=1>>[CH3:1][O:2][P:3]([CH2:13][C:12]1[CH:15]=[CH:16][C:9]([Cl:8])=[CH:10][CH:11]=1)(=[O:6])[O:4][CH3:5]

Participants

3

Reactant 2

HCID 8472Trimethyl phosphiteHCID 693291-(Bromomethyl)-4-chlorobenzene

Product 1

HCID 12266546(4-chlorobenzyl)-phosphonic acid dimethyl esterYield 93%

Procedure

To a stirred solution of trimethylphosphite (0.57 ml, 4.9 mmol) was added 4-chlorobenzylbromide (1.0 g, 4.9 mmol) at rt. The resulting mixture was stirred at rt for 5 min. and then heated in an oil bath at 80° C. for 20 min. It was cooled to rt and the product purified on a silica-gel column with 25% EtOAc in hexane to give 1.05 g of (4-chloro-benzyl)-phosphonic acid dimethyl ester (93%).

Workup

  1. temperatureheated in an oil bath at 80° C. for 20 min
  2. temperatureIt was cooled to rt
  3. customthe product purified on a silica-gel column with 25% EtOAc in hexane

Sources & evidence

ORD record
ord-eb248a4f42a842708b15e43336f8ae83
Source dataset
uspto-grants-2006_07
Patent number
US07081531B2

Reaction notes

Loading…