Triethyl phosphite → HCID 25149509, compound

HRID 1170976Notes

Reaction equation

HRID 1170976 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:22])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([CH:19]([CH3:21])[CH3:20])[CH:12]=1)[CH2:5]Br.[CH2:23]([O:25][P:26]([O:30]CC)[O:27][CH2:28][CH3:29])[CH3:24]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:22])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([CH:19]([CH3:21])[CH3:20])[CH:12]=1)[CH2:5][P:26](=[O:30])([O:27][CH2:28][CH3:29])[O:25][CH2:23][CH3:24]

Participants

5

Reactant 2

HCID 31215Triethyl phosphiteHCID 25150222HCID 25150222, compound

Product 1

HCID 25149509HCID 25149509, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3,5-dichloro-4-(3′-iso-propyl-4′-methoxyphenoxy)benzyl bromide (0.61 g, 1.51 mmol) and triethylphosphite (0.61 g, 3.56 mmol) in DMF (2.0 mL) was heated under reflux for 4 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and washed with water and brine. The organic layer was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with acetone-hexanes (3:7) to afford diethyl 3,5-dichloro-4-(3′-iso-propyl-4′-methoxyphenoxy)benzylphosphonate as an oil (0.59 g, 85%): 1H NMR (300 MHz, DMSO-d6): δ 7.55 (s, 2 H), 6.88 (d, J=9.0 Hz, 1 H), 6.75 (d, J=3.0 Hz, 1 H), 6.43 (m, 1 H), 4.01 (m, 4 H), 3.75 (s, 3 H), 3.41 (m, 2 H), 3.22 (m, 1 H), 1.20 (m, 6 H), 1.12 (d, J=6.0 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=hexanes-ethyl acetate (4:1); Rf=0.22.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. washwashed with water and brine
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel
  6. washeluting with acetone-hexanes (3:7)

Sources & evidence

ORD record
ord-2d0872bcfa7245a5b02ce1a019c3e6cb
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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