Triethyl phosphite → Diethyl 3-iodobenzylphosphonate

HRID 2357134Notes

Reaction equation

HRID 2357134 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[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:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 27593613-Iodobenzyl bromide

Product 1

HCID 58999960Diethyl 3-iodobenzylphosphonateYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 3-iodobenzyl bromide 12 (5 g, 16.84 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 5.4 g of 13 (91%). 1H NMR (200 MHz, CDCl3): δ 1.15 (t, J=7.05 Hz, 6H), 2.97 (d, J=21.65 Hz, 2H), 3.92 (m, 4H), 6.93 (t, J=7.76 Hz, 1H), 7.17 (m, 1H), 7.52 (m, 2H); 13C NMR (50 MHz, CDCl3): 16.25 (J=5.95 Hz), 33.15 (J=137.60 Hz), 62.19 (J=6.70 Hz), 94.13 (J=3.50 Hz), 128.89 (J=6.35 Hz), 130.07 (J=3.00 Hz), 133.95 (J=9.10 Hz), 135.87 (J=3.55 Hz), 138.51 (J=6.65 Hz).

Workup

  1. temperaturethe mixture was cooled to room temperature

Sources & evidence

ORD record
ord-c3fbb3d653454a45b1424d7d3f6425ad
Source dataset
uspto-grants-2010_07
Patent number
US07759502B2

Reaction notes

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