Triethyl phosphite → (2-Chloro-5-methoxy-4 nitrobenzyl)-phosphonic acid diethylester

HRID 2279873Notes

Reaction equation

HRID 2279873 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([N+:11]([O-:13])=[O:12])=[CH:5][C:4]=1[Cl:14].ClC1C=C([N+]([O-])=O)C(OC)=CC=1C.ClC1C=C([N+]([O-])=O)C(OC)=CC=1C(Br)Br.[CH2:43]([O:45][P:46]([O:50]CC)[O:47][CH2:48][CH3:49])[CH3:44]>C1(C)C=CC=CC=1>[CH2:43]([O:45][P:46]([CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([N+:11]([O-:13])=[O:12])=[CH:5][C:4]=1[Cl:14])(=[O:50])[O:47][CH2:48][CH3:49])[CH3:44]

Participants

6

Reactant 4

HCID 31215Triethyl phosphiteHCID 158645661-Chloro-4-methoxy-2-methyl-5-nitrobenzeneHCID 678139681-(Bromomethyl)-2-chloro-5-methoxy-4-nitrobenzeneHCID 678145601-Chloro-2-dibromomethyl-4-methoxy-5-nitro-benzene2×

Product 1

HCID 86697809(2-Chloro-5-methoxy-4 nitrobenzyl)-phosphonic acid diethylester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-Bromomethyl-2-chloro-5-methoxy-4-nitro-benzene, 1-Chloro-4-methoxy-2-methyl-5-nitro-benzene and 1-chloro-2-dibromomethyl-4-methoxy-5-nitro-benzene (Compound 56G, 24 g, 1:015:0.5) in toluene (100 mL) were treated with triethylphosphite (15.6 g, 94.2 mmol) and heated to reflux for 24 hrs. Toluene and triethylphosphite were distilled off under reduced pressure. The residue was treated with hot diisopropyl ether to give 10 g of the required compound as dark yellow crystals.

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hrs
  3. distillationToluene and triethylphosphite were distilled off under reduced pressure
  4. additionThe residue was treated with hot diisopropyl ether

Sources & evidence

ORD record
ord-99404d6ffef2434da3fcdc67602480b5
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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