Triethyl phosphite → Diethyl ((4-iodophenyl)methyl)phosphonate

HRID 1297534Notes

Reaction equation

HRID 1297534 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[P:10]([O:17]CC)([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13]>CCOC(C)=O>[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 9542584-Iodobenzyl bromide

Product 1

HCID 15166405Diethyl ((4-iodophenyl)methyl)phosphonateYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 4-iodobenzyl bromide 14 (5.2 g, 17.51 mmol) and triethyl phosphite (3.3 g, 20 mmol) was stirred at 160° C. After 4 h, the mixture was cooled to room temperature. The residue was subjected to flash chromatography (EtOAc: Hex, 1:4), and gave 3.27 g of 15 (53%). 1H NMR (200 MHz, CDCl3): δ1.24 (t, J=7.04 Hz, 6H), 3.07 (d, J=21.72 Hz, 2H), 4.01 (m, 4H), 7.04 (m, 2H), 7.62 (m, 2H); 13C NMR (50 MHz, CDCl3): δ 16.24 (J=5.90 Hz), 33.21 (J=137.55 Hz), 62.04 (J=6.70 Hz), 92.15 (J=4.80 Hz), 131.31 (J=9.10 Hz), 131.57 (J=6.55 Hz), 137.43 (J=2.95 Hz).

Workup

  1. temperaturethe mixture was cooled to room temperature

Sources & evidence

ORD record
ord-f2a9eb5d1105471aa255f44e496e209f
Source dataset
uspto-grants-2007_07
Patent number
US07250525B2

Reaction notes

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