Triethyl phosphite → Diethyl 2-chloro-3-methoxy-4-nitrobenzylphosphonate

HRID 2279865Notes

Reaction equation

HRID 2279865 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([O:12][CH3:13])[C:4]=1[Cl:14].[CH2:15]([O:17][P:18]([O:22]CC)[O:19][CH2:20][CH3:21])[CH3:16]>C1(C)C=CC=CC=1>[Cl:14][C:4]1[C:5]([O:12][CH3:13])=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[CH2:2][P:18](=[O:22])([O:19][CH2:20][CH3:21])[O:17][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 678125961-(Bromomethyl)-2-chloro-3-methoxy-4-nitrobenzene2×

Product 1

HCID 86697802Diethyl 2-chloro-3-methoxy-4-nitrobenzylphosphonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-(bromomethyl)-2-chloro-3-methoxy-4-nitrobenzene (Compound 54G, 900 mg, 3.21 mmol) in toluene (10 mL) was added triethylphosphite (586 mg, 3.53 mmol) and heated to reflux for 24 h. Toluene and triethylphosphite were distilled off under reduced pressure to provide the desired compound, 800 mg (79%). 1H NMR (300 MHz, CDCl3) δ 7.77 (d, 1H), 7.35 (d, 1H), 4.19-4.05 (m, 4H), 4.00 (s, 3H), 3.43 (d, 2H), 1.31 (t, 6H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 h
  3. distillationToluene and triethylphosphite were distilled off under reduced pressure

Sources & evidence

ORD record
ord-89b07ca0e2634f738c9f844f9039b6f1
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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