Triethylamine → 5-Bromo-2-(trifluoromethoxy)benzonitrile

HRID 1747508ノート

反応式

HRID 1747508 の反応式
C([N:3]([CH2:6][CH3:7])CC)C.CCCP(=O)=O.[Br:14][C:15]1[CH:16]=C[C:18]([O:23][C:24]([F:27])([F:26])[F:25])=[C:19]([CH:22]=1)C=O.Cl.ON.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:14][C:15]1[CH:22]=[CH:19][C:18]([O:23][C:24]([F:25])([F:26])[F:27])=[C:7]([CH:16]=1)[C:6]#[N:3]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 16167369Propylphosphoric anhydrideHCID 265992015-Bromo-2-(trifluoromethoxy)benzaldehyde

生成物 1

HCID 451081625-Bromo-2-(trifluoromethoxy)benzonitrile収率 86.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

Triethylamine (1.14 mL, 8.18 mmol) and propylphosphonic anhydride (cyclic trimer) (ca. 1.7 M solution in ethyl acetate, 4.8 mL, 8.18 mmol) were added in this order to a solution of 5-bromo-2-(trifluoromethoxy)benzaldehyde (2.00 g, 7.43 mmol) and hydroxyamine hydrochloride (568 mg, 8.18 mmol) in DMF (7.5 mL), and the mixture was stirred at 100° C. for 8 hours. The reaction solution was poured to a saturated sodium bicarbonate aqueous solution, followed by extraction with ethyl acetate. The obtained organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=100/0-98/2] to obtain the title compound (1.71 g, yield: 86%).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe obtained organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=100/0-98/2]

出典と根拠

ORDレコード
ord-fbffe86c42274eaba2b208d8911af331
出典データセット
uspto-grants-2015_10
特許番号
US09150575B2

反応ノート

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