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

HRID 474689ノート

反応式

HRID 474689 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred suspension of methyltriphenylphosphonium bromide (3.85 g, 10.77 mmol) and KOt-Bu (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

後処理

  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

出典と根拠

ORDレコード
ord-87f36b816d354c569af878fef1c4eb1b
出典データセット
uspto-grants-2014_01
特許番号
US08637536B2

反応ノート

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