Ethanol → 1-Bromo-3-isopropylbenzene

HRID 269455

反応式

HRID 269455 の反応式
C(O)C.OS(O)(=O)=O.[Br:9][C:10]1[CH:16]=[C:15]([CH:17]([CH3:19])[CH3:18])[CH:14]=[CH:13][C:11]=1N.N([O-])=O.[Na+]>O.[Cu]>[Br:9][C:10]1[CH:11]=[CH:13][CH:14]=[C:15]([CH:17]([CH3:19])[CH3:18])[CH:16]=1

参加物

7

反応物 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 5213372-Bromo-4-isopropylanilineHCID 23668193Sodium Nitrite

生成物 1

HCID 1384991-Bromo-3-isopropylbenzene

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 962Water溶媒

反応条件

温度
-5 °C

実験手順

To a mixture of 1000 ml of 96% ethanol and 94 ml of 98% H2SO4, 117 g (0.55 mol) of 2-bromo-4-isopropylaniline was added, while vigorously stirring, at −5° C. over 15 min. Then, a solution of 63 g of NaNO2 in 125 ml of water was added at this temperature over 1 h, and the resulting mixture was stirred for about 30 min longer. Then, 12 g of copper powder was added. The reaction mixture was refluxed for 4 h and then filtered through a glass frit (G3). The filtrate was poured into 2500 cm3 of cold water. The organic product was extracted with 4×400 ml of dichloromethane. The combined extract was dried over K2CO3 and evaporated to dryness. Fractional distillation gave the title product, b.p. 64-67° C./3 mm Hg. Yield 117.4 g (75%) of yellowish oil.

後処理

  1. additionwas added
  2. stirringthe resulting mixture was stirred for about 30 min longer
  3. temperatureThe reaction mixture was refluxed for 4 h
  4. filtrationfiltered through a glass frit (G3)
  5. additionThe filtrate was poured into 2500 cm3 of cold water
  6. extractionThe organic product was extracted with 4×400 ml of dichloromethane
  7. extractionThe combined extract
  8. dry with materialwas dried over K2CO3
  9. customevaporated to dryness
  10. distillationFractional distillation

出典と根拠

ORDレコード
ord-7470b2ec66324608845d5208c81ae316
出典データセット
uspto-grants-2008_11
特許番号
US07446216B2

関連ノート

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