Triethyl phosphite → HCID 73012130, compound

HRID 2041839Notes

Reaction equation

HRID 2041839 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1I.[CH2:10]([O:12][P:13]([O:17]CC)[O:14][CH2:15][CH3:16])[CH3:11]>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[P:13](=[O:17])([O:14][CH2:15][CH3:16])[O:12][CH2:10][CH3:11]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 27827381,3-Difluoro-2-iodobenzene

Product 1

HCID 73012130HCID 73012130, compoundYield 74%

Procedure

2,6-difluoroiodobenzene (3.0 g, 12.5 mmol) was combined with triethylphosphite (10.7 mL, 62.5 mmol) in a pressure vessel which had been flushed with nitrogen. The vessel was sealed and rotated in the photoreactor (16 bulbs-350 nm) for 20 hours. The reaction mixture was put under hi-vacuum (0.08 Torr) at 50° C. for 5 hours. A column was run in hexanes and ethyl acetate (increasing polarity as run). The top spot, which was UV active, was separated. After removing solvent, a yellow-tinted liquid was left (2.30 g, 74% yield). 1H NMR (400.14 MHz, DMSO) δ 7.72 (m), 7.21 (m, 2H), 4.10 (m, 4H), 1.25 (t, J=7.04 Hz). 31P{1H} NMR (161.97 MHz, DMSO): δ 8.23. The phosphonate can be hydrolyzed as described above to provide the corresponding phosphonic acid.

Workup

  1. customwhich had been flushed with nitrogen
  2. customThe vessel was sealed
  3. waitThe reaction mixture was put under hi-vacuum (0.08 Torr) at 50° C. for 5 hours
  4. customwas separated
  5. customAfter removing solvent
  6. waita yellow-tinted liquid was left (2.30 g, 74% yield)

Sources & evidence

ORD record
ord-607c16cdb7a34ab7be0b237c8853dbc3
Source dataset
uspto-grants-2013_11
Patent number
US08586208B2

Reaction notes

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