Triethyl phosphite → Diethyl 4-nitrobenzylphosphonate

HRID 45641Notes

Reaction equation

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

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 660114-Nitrobenzyl bromide

Product 1

HCID 256065Diethyl 4-nitrobenzylphosphonateYield 89%

Conditions

Temperature: 110 °C

Procedure

Into a 250-mL round-bottom flask, was placed 1-(bromomethyl)-4-nitrobenzene (15 g, 69.77 mmol, 1.00 equiv), triethyl phosphite (70 mL). The resulting solution was stirred for 2 h at 110° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10-1:1). This resulted in 17 g (89%) of the title compound as a yellow oil.

Workup

customInto a 250-mL round-bottom flask, was placed
concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record: ord-d424663ee781470495ffa60bf9c771e2
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541448B2

Reaction notes

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