3-Fluoro-4-((6-(trifluoromethyl)pyridin-2-yl)oxy)benzaldehyde → 2-(2-Fluoro-4-vinylphenoxy)-6-(trifluoromethyl)pyridine

HRID 705919Notes

Reaction equation

HRID 705919 reaction equation
[Li][CH2:2]CCC.[F:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]=1)[CH:10]=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.CC(=O)OCC>[F:6][C:7]1[CH:8]=[C:9]([CH:10]=[CH2:2])[CH:12]=[CH:13][C:14]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]=1

Participants

6

Reactant 2

HCID 866662133-Fluoro-4-((6-(trifluoromethyl)pyridin-2-yl)oxy)benzaldehydeHCID 178418339Butyllithium

Product 1

HCID 677762762-(2-Fluoro-4-vinylphenoxy)-6-(trifluoromethyl)pyridineYield 50.8%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyltriphenylphosphonium bromide (1226 mg, 3.43 mmol) in THF (15 mL) was added n-BuLi (2.145 mL, 3.43 mmol), stirred for 10 min. then 3-fluoro-4-((6-(trifluoromethyl)pyridin-2-yl)oxy)benzaldehyde (0.691 mL, 3.12 mmol) was added. The mixture was stirred at 0° C. for 1 h, then at room temperature for another 2 h. The reaction mixture was diluted with EA, washed with water, brine (50 mL), and concentrated. The residue was purified via flash chromatography to afford the title compound (449 mg, 49.8% yield) as colorless oil. LCMS: rt=3.13 min

Workup

  1. stirringThe mixture was stirred at 0° C. for 1 h
  2. waitat room temperature for another 2 h
  3. washwashed with water, brine (50 mL)
  4. concentrationconcentrated
  5. customThe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-887c4acb0251413598f0df6cdd0d9304
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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