Trimethyl phosphite → (4-methylsulfanyl-benzyl)-phosphonic acid dimethyl ester

HRID 1440951Notes

Reaction equation

HRID 1440951 reaction equation
[CH3:1][O:2][P:3]([O:6]C)[O:4][CH3:5].[CH3:8][S:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][CH:11]=1>>[CH3:8][S:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][P:3](=[O:6])([O:4][CH3:5])[O:2][CH3:1])=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 8472Trimethyl phosphiteHCID 701281-(Chloromethyl)-4-(methylthio)benzene

Product 1

HCID 10955842(4-methylsulfanyl-benzyl)-phosphonic acid dimethyl ester

Procedure

First, dimethyl (4-methylthiobenzyl)phosphonate was synthesized, as follows: Trimethylphosphite (206 g, 1.66 mol) was stirred at reflux, and 245 g (1.42 mol) of 4-methylmercaptobenzyl chloride (prepared as described in Ulman, et al. U.S. Pat. No. 4,792,208, Example 1) was added dropwise over 30 min. The mixture was kept at reflux for 4 hours, and then cooled to room temperature. Dimethyl (4-methylthiobenzyl)phosphonate was obtained by fractional distillation at reduced pressure. The yield was 263 grams, which is 75% of theoretical.

Workup

  1. customFirst, dimethyl (4-methylthiobenzyl)phosphonate was synthesized
  2. temperatureat reflux
  3. addition4,792,208, Example 1) was added dropwise over 30 min
  4. temperatureat reflux for 4 hours

Sources & evidence

ORD record
ord-1910a60a5625469e9b9c1e66a48ea214
Source dataset
uspto-grants-1996_03
Patent number
US05501821

Reaction notes

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