Triethyl Phosphate → Diethyl 2-chloro-5-fluoro-4-nitrobenzylphosphonate

HRID 515300Notes

Reaction equation

HRID 515300 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([F:9])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][C:4]=1[Cl:13].[P:14](OCC)([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15]>>[Cl:13][C:4]1[CH:5]=[C:6]([N+:10]([O-:12])=[O:11])[C:7]([F:9])=[CH:8][C:3]=1[CH2:2][P:14](=[O:15])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18]

Participants

3

Reactant 2

HCID 6535Triethyl PhosphateHCID 67190633HCID 67190633, compound

Product 1

HCID 86670949Diethyl 2-chloro-5-fluoro-4-nitrobenzylphosphonate

Procedure

1-(Bromomethyl)-2-chloro-5-fluoro-4-nitrobenzene (6.7 g, 18.62 mmol) and triethyl phosphate (5.64 mL) were heated in an oil bath for 3 hours at 140° C. The reaction mixture was concentrated and chromatographed on silica eluting with dichloromethane/methanol (1:0-1%) to give the title compound (4.06 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customchromatographed on silica eluting with dichloromethane/methanol (1:0-1%)

Sources & evidence

ORD record
ord-c0ff06039a09482c8269c727240d8ac1
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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