Triisopropyl phosphite → Dipropan-2-yl [(4-nitrophenyl)methyl]phosphonate

HRID 1794343Notes

Reaction equation

HRID 1794343 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:21]C(C)C)([O:17][CH:18]([CH3:20])[CH3:19])[O:13][CH:14]([CH3:16])[CH3:15]>>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][P:12](=[O:21])([O:17][CH:18]([CH3:20])[CH3:19])[O:13][CH:14]([CH3:16])[CH3:15])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 8304Triisopropyl phosphiteHCID 660114-Nitrobenzyl bromide

Product 1

HCID 13427619Dipropan-2-yl [(4-nitrophenyl)methyl]phosphonateYield 93.2%

Procedure

A mixture of 4-nitrobenzylbromide (15.0 g) and triisopropyl phosphite (15.9 g) was stirred for 3 hr while heating under reflux. The reaction mixture was subjected to silica gel column chromatography, and diisopropyl 4-nitrobenzylphosphonate (19.5 g) was obtained as an oil from a fraction eluted with ethyl acetate-chloroform (1:1, volume ratio). A mixture of this oil, 5% palladium-carbon (2.3 g) and ethanol (130 ml) was stirred at room temperature for 6 hr under a hydrogen atmosphere. The catalyst was filtered off and the filtrate (ethanol solution) was concentrated to give diisopropyl 4-aminobenzylphosphonate (17.2 g, yield 98%) as a yellow oil.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux

Sources & evidence

ORD record
ord-3beae4971a5f49fe873172dcf3e38bc9
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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