Triethyl phosphite → HCID 86673423, compound

HRID 2362381Notes

Reaction equation

HRID 2362381 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[F:10].[P:11]([O:18]CC)([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14]>>[F:10][C:4]1[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:3]=1[CH2:2][P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 5228302-(Bromomethyl)-1,4-difluorobenzene

Product 1

HCID 86673423HCID 86673423, compoundYield 93.3%

Conditions

Temperature
160 °C

Procedure

A mixture of 2-(bromomethyl)-1,4-difluorobenzene (3 g, 14.49 mmol) and triethyl phosphite (7.72 ml, 43.5 mmol) was heated to 160° C. with stirring for 4 hours, cooled to ambient temperature and concentrated under high vacuum to remove most triethyl phosphite. The resulting residue was purified by column chromatography (20% to 30% EtOAc/Toluene) providing diethyl 2,5-difluorobenzylphosphonate (3.76 g, 13.52 mmol, 93% yield) as colorless oil. 1H NMR (500 MHz, DMSO-d6) δ 7.30-7.10 (m, 3H), 4.05-3.91 (m, 4H), 3.31-3.20 (m, 2H), 1.18 (t, J=7.0 Hz, 6H). MS Anal. Calcd. for [M+H]+ C11H16F2O3P: 265.2. found 265.3.

Workup

  1. temperaturecooled to ambient temperature
  2. concentrationconcentrated under high vacuum
  3. customto remove most triethyl phosphite
  4. customThe resulting residue was purified by column chromatography (20% to 30% EtOAc/Toluene)

Sources & evidence

ORD record
ord-fdfc2485f1064bbfa40b6e8c66a97153
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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