Triethyl phosphite → Diethyl 3-Nitrobenzylphosphonate

HRID 515362Notes

Reaction equation

HRID 515362 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[P:12]([O:19]CC)([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]>>[N+:9]([C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])([O-:11])=[O:10]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 13675396Diethyl 3-NitrobenzylphosphonateYield 63.2%

Conditions

Temperature
100 °C

Procedure

A stirring suspension of 1-(bromomethyl)-3-nitrobenzene (46.3 mmol, 10 g) in triethyl phosphite (69.4 mmol, 12.08 mL, 11.54 g) was heated at 100° C. for 4 hours. The reaction mixture was cooled to room temperature and partitioned between water and dichloromethane. The organic layer was separated, dried and concentrated under vacuum. The residue was purified by silica column chromatography (eluent: 0-5% methanol in dichloromethane) to afford the title compound (8 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between water and dichloromethane
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica column chromatography (eluent: 0-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f5d4e3ab923b4cd2894c8198177f9663
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

Loading…