Triphenylphosphine → HCID 117678569, compound

HRID 1522953Notes

Reaction equation

HRID 1522953 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH3:10])[CH:5]=[C:4]([F:11])[C:3]=1[OH:12].[F:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([F:22])[CH:21]=1)[CH2:17]O.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>O.C1COCC1>[F:13][C:14]1[CH:15]=[C:16]([CH2:17][O:12][C:3]2[C:2]([F:1])=[CH:7][C:6]([CH2:8][CH2:9][CH3:10])=[CH:5][C:4]=2[F:11])[CH:19]=[C:20]([F:22])[CH:21]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5227213,5-Difluorobenzyl alcoholHCID 5363146Diisopropyl azodicarboxylateHCID 18979655HCID 18979655, compound

Product 1

HCID 117678569HCID 117678569, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

Into THF (85 mL), 2,6-difluoro-4-propylphenol obtained in (1-2) in Example 1 (17.2 g), 3,5-difluorobenzyl alcohol (17.2 g), triphenylphosphine (28.9 g) were dissolved, and the product was cooled to −10° C. DIAD (21.2 g) was added thereto at a rate which did not allow the internal temperature to exceed 15° C., and the product was stirred for 3 hours at room temperature. Then, 5 mL of water was added thereto, the solvent was distilled off under reduced pressure, hexane (300 mL) was added thereto, and the product was stirred. The precipitate was removed by filtration, the filtrate was washed with an aqueous solution of 50% methanol (200 mL) and a saturated salt solution in sequence, and sodium sulfate was added thereto for dehydration. The solvent was distilled off under reduced pressure, and the product was purified by silica gel column chromatography, thereby yielding a slightly yellow liquid that what 1,3-difluoro-5-[(2,6-difluoro-4-propylphenyloxy)methyl]benzene (19.1 g).

Workup

  1. dissolutionwere dissolved
  2. customto exceed 15° C.
  3. distillationthe solvent was distilled off under reduced pressure, hexane (300 mL)
  4. additionwas added
  5. stirringthe product was stirred
  6. customThe precipitate was removed by filtration
  7. washthe filtrate was washed with an aqueous solution of 50% methanol (200 mL)
  8. additiona saturated salt solution in sequence, and sodium sulfate was added
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3f6ab1d5879f4e63bc06666ab2082107
Source dataset
uspto-grants-2015_07
Patent number
US09079836B2

Reaction notes

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