Triethyl phosphite → Phosphonic acid, P-[(3-bromo-2-ethylphenyl)methyl]-, diethyl ester

HRID 1942699Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[C:3]=1[CH2:10][CH3:11].[P:12]([O:19]CC)([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([CH2:10][CH3:11])=[C:4]([CH2:8][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 1-bromo-3-(bromomethyl)-2-ethylbenzene (D134) (1.3 g, 4.68 mmol) in Toluene (10 mL) was added triethyl phosphite (0.818 mL, 4.68 mmol). The reaction solution was heated in a sealed tube at 130° C. for 2 days. The solvent was removed in vacuo to afford diethyl [(3-bromo-2-ethylphenyl)methyl]phosphonate (D135) (1.567 g), which was used directly without further purification. MS (ES): C13H20BrO3P requires 334.0. found 335.0 (M+H+).

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-41b97cdf284a4a97b522d353ee0139d4
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389508B2

Reaction notes

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