Triethyl phosphite → Diethyl 3-chloro-4-nitrobenzylphosphonate

HRID 515310Notes

Reaction equation

HRID 515310 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([Cl:12])[CH:4]=1.[P:13]([O:20]CC)([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16]>>[Cl:12][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[N+:9]([O-:11])=[O:10])[CH2:2][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 671933714-(Bromomethyl)-2-chloro-1-nitrobenzene

Product 1

HCID 86654007Diethyl 3-chloro-4-nitrobenzylphosphonateYield 48%

Conditions

Temperature
100 °C

Procedure

4-(Bromomethyl)-2-chloro-1-nitrobenzene (17.21 mmol, 4.31 g) and triethyl phosphite (25.8 mmol, 4.34 mL, 4.29 g) were combined and heated to 100° C. for 4 hours. The reaction mixture was quenched with water and extracted into ether. The organic phase was concentrated under vacuum. The resulting residue was purified by silica chromatography (eluting with dichloromethane-2% dichloromethane/methanol) to give the intermediate diethyl 3-chloro-4-nitrobenzylphosphonate (2.54 g).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted into ether
  3. concentrationThe organic phase was concentrated under vacuum
  4. customThe resulting residue was purified by silica chromatography (eluting with dichloromethane-2% dichloromethane/methanol)

Sources & evidence

ORD record
ord-6ea87df4ba9246f685f279b775a66560
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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