Isopropanol → 4-[(E)-2-cyclohexylethenyl]-2-fluoroaniline

HRID 576079ノート

反応式

HRID 576079 の反応式
C(O)(C)C.C(O[K])(C)(C)C.[CH:11]1(/[CH:17]=[CH:18]/B(O)O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.Br[C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([F:30])[CH:24]=1>ICCC.O>[CH:11]1(/[CH:17]=[CH:18]/[C:23]2[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([F:30])[CH:24]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

参加物

7

反応物 4

HCID 3776IsopropanolHCID 1230504-Bromo-2-fluoroanilineHCID 6031024(2-Cyclohexylvinyl)boronic acidHCID 178418922HCID 178418922、化合物

生成物 1

HCID 867072824-[(E)-2-cyclohexylethenyl]-2-fluoroaniline収率 99.7%

試薬・触媒・溶媒 2

HCID 336431-Iodopropane触媒HCID 962Water溶媒

実験手順

Isopropanol (60 mL) was added to PEPPSI™-IPr catalyst (161 mg, 0.24 mmol) and tert-butoxy potassium (2.65 g, 23.6 mmol) under an argon atmosphere, and the mixture was stirred at room temperature for 15 min. To the reaction mixture were added trans-(2-cyclohexylvinyl)boronic acid (2.00 g, 13.0 mmol) and 4-bromo-2-fluoroaniline (2.24 g, 11.8 mmol) successively and the mixture was stirred at room temperature for 15 hr. Water was added thereto, the mixture was extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure to afford 4-[(E)-2-cyclohexylethenyl]-2-fluoroaniline as a reddish brown oil (2.58 g).

後処理

  1. stirringthe mixture was stirred at room temperature for 15 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe desiccant was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-c09a1b39f8f547cabadb0c5a76a78547
出典データセット
uspto-grants-2015_05
特許番号
US09035059B2

反応ノート

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