Triphenylphosphine → HCID 90410612, compound

HRID 1406835Notes

Reaction equation

HRID 1406835 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)[CH:7]=[C:6]([F:19])[C:3]=1[CH2:4][OH:5].[F:20][C:21]1[CH:22]=[C:23](O)[CH:24]=[C:25]([F:28])[C:26]=1[F:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[F:20][C:21]1[CH:22]=[C:23]([O:5][CH2:4][C:3]2[C:2]([F:1])=[CH:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH3:18])=[CH:12][CH:11]=3)=[CH:7][C:6]=2[F:19])[CH:24]=[C:25]([F:28])[C:26]=1[F:27]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 27779433,4,5-TrifluorophenolHCID 5363146Diisopropyl azodicarboxylateHCID 90411281HCID 90411281, compound

Product 1

HCID 90410612HCID 90410612, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a nitrogen atmosphere, 10.00 g of 2,6-difluoro-4-(4-propylphenyl)benzyl alcohol, 5.65 g of 3,4,5-trifluorophenol, and 13.01 g of triphenylphosphine were dissolved in 30 mL of THF, the resultant solution was cooled to −20° C., and 8.48 g of DIAD was added dropwise at such a rate that the inside temperature did not exceed −10° C. After stirring at room temperature for 1 hour, the solvent was distilled off under reduced pressure. Then, the residue was suspended by adding hexane, and precipitated triphenylphosphine was filtered off. An organic layer was washed with saturated brine and dried by adding sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography and then recrystallized from ethanol to yield 11.32 g of (3,4,5-trifluorophenyloxy)-[2,6-difluoro-4-(4-propylphenyl)phenyl]methane.

Workup

  1. customdid not exceed −10° C
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionby adding hexane
  4. customprecipitated triphenylphosphine
  5. filtrationwas filtered off
  6. washAn organic layer was washed with saturated brine
  7. customdried
  8. additionby adding sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3bb57aba63df4cce95c884a2e675f84a
Source dataset
uspto-grants-2014_12
Patent number
US08916718B2

Reaction notes

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