Tetrahydrofuran → 5-(2-Fluoro-4-vinylphenoxy)-2-(trifluoromethyl)pyrimidine

HRID 705923Notes

Reaction equation

HRID 705923 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:12]=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[N:15][CH:16]=1)[CH:5]=O.[H-].[Na+].[CH2:23]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH2:23])[CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:12]=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 866662143-Fluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)benzaldehyde

Product 1

HCID 677766905-(2-Fluoro-4-vinylphenoxy)-2-(trifluoromethyl)pyrimidineYield 27.2%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

To a stirred suspension of 3-fluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)benzaldehyde (2 g, 6.99 mmol) and methyltriphenylphosphonium bromide (2.496 g, 6.99 mmol) in dry THF (40 mL) was added NaH (0.978 g, 24.46 mmol) under nitrogen at 0° C. The mixture was stirred at room temperature for 4 h. The organic layer was washed three times with brine, dried over Na2SO4, filtered, and concentrated. Purification via flash chromatography afforded the title compound (540 mg, 1.900 mmol, 27.2% yield). LCMS: rt=3.65 min, [M+H+]=285

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-6ceb87c91244460a87cf1b7484a5e69c
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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