Triethyl phosphite → Diethyl 4-nitrobenzylphosphonate

HRID 1827426Notes

Reaction equation

HRID 1827426 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[P:12]([O:19]CC)([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]>CN(C)C=O.O>[CH2:14]([O:13][P:12]([CH2:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:19])[O:16][CH2:17][CH3:18])[CH3:15]

Participants

5

Reactant 2

HCID 31215Triethyl phosphiteHCID 660114-Nitrobenzyl bromide

Product 1

HCID 256065Diethyl 4-nitrobenzylphosphonateYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

10 g (46.3 mmol) of 4-nitrobenzylbromide and 10.03 g (60.3 mmol) of triethyl phosphite are dissolved in 25 ml dimethylformamide. The reaction mixture is held at 155° C. for 1.5 h, diluted with 20 ml water and extracted 3 times with ethyl acetate. The organic phase is dried and concentrated to yield 8.35 g (66%) of the crude title compound. MS: m/e=274.1 (M++H).

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. customThe organic phase is dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6975fad7f17f4f2ea5dc81efe261a67c
Source dataset
uspto-grants-2006_05
Patent number
US07053245B2

Reaction notes

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