Ammonium Chloride → 5-(2,6-Difluoro-4-vinylphenoxy)-2-(trifluoromethyl)pyrimidine

HRID 705926Notes

Reaction equation

HRID 705926 reaction equation
[CH3:1]C([O-])(C)C.[K+].[F:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([F:27])[C:15]=1[O:16][C:17]1[CH:18]=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[N:21][CH:22]=1)[CH:11]=O.[NH4+].[Cl-]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[F:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH2:1])[CH:13]=[C:14]([F:27])[C:15]=1[O:16][C:17]1[CH:18]=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[N:21][CH:22]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 866662153,5-Difluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)benzaldehyde

Product 1

HCID 677743945-(2,6-Difluoro-4-vinylphenoxy)-2-(trifluoromethyl)pyrimidineYield 54.2%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of methyltriphenylphosphonium bromide (3.85 g, 10.77 mmol) and KOtBu (1.309 g, 11.67 mmol) in dry THF (50 mL), which was stirred at room temperature for 1 h under nitrogen, was added 3,5-difluoro-4-((2-(trifluoromethyl) pyrimidin-5-yl)oxy)benzaldehyde (2.73 g, 8.98 mmol). The mixture was stirred at room temperature for 3 h. The reaction mixture was neutrilized with sat. NH4Cl. The aqueous phase was extracted with EA. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification via flash chromatography afforded the title compound (1.47 g, 4.86 mmol, 54.2% yield) as a yellow oil. LCMS: rt=3.72 min, [M+H+]=303

Workup

  1. stirringThe mixture was stirred at room temperature for 3 h
  2. extractionThe aqueous phase was extracted with EA
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via flash chromatography

Sources & evidence

ORD record
ord-27805ed1379d41519e3830346a35fd18
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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