Tetrahydrofuran → 1-Chloro-3-[(4-ethenylphenyl)oxy]-5-(trifluoromethyl)benzene

HRID 474677Notes

Reaction equation

HRID 474677 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[H-].[Na+].[CH2:23]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([O:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[CH2:23])=[CH:15][CH:14]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 866662124-{[3-Chloro-5-(trifluoromethyl)phenyl]oxy}benzaldehyde

Product 1

HCID 677769391-Chloro-3-[(4-ethenylphenyl)oxy]-5-(trifluoromethyl)benzeneYield 80%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

To a stirred suspension of 4-{[3-chloro-5-(trifluoromethyl)phenyl]oxy}benzaldehyde (3.3 g, 10.98 mmol) and methyl(triphenyl)phosphonium bromide (3.92 g, 10.98 mmol) in dry THF (30 mL) was added NaH (1.536 g, 38.4 mmol) under nitrogen at 0° C. The mixture was stirred at room temperature for 2 h. The organic layer was washed three times with brine, dried over Na2SO4, filtered, and concentrated. Purification via flash chromatography afforded the title compound (2.63 g, 8.81 mmol, 80% yield) as a light green oil. LCMS: rt=4.45 min, [M+H+]=324

Workup

  1. washThe organic layer was washed three times with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification via flash chromatography

Sources & evidence

ORD record
ord-5a92caf66ccf447fac185f37a48ddeca
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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