Iodoethane → (4-Bromo-2-tert-butylphenyl)diethylamine

HRID 1698394ノート

反応式

HRID 1698394 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH3:10])=[C:4]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=1.[H-].[Na+].I[CH2:18][CH3:19].[Cl-].[NH4+]>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:18][CH3:19])[CH2:9][CH3:10])=[C:4]([C:11]([CH3:13])([CH3:12])[CH3:14])[CH:3]=1

参加物

6

反応物 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 66671970HCID 66671970、化合物

生成物 1

HCID 66671963(4-Bromo-2-tert-butylphenyl)diethylamine収率 63.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
0 °C

実験手順

5 g (20 mmol) of (4-bromo-2-tert-butylphenyl)-ethylamine are dissolved, under a stream of nitrogen, in 200 ml of DMSO. After cooling to 0° C., 1.7 g (43 mmol) of sodium hydride are added slowly. After 30 minutes, 3.4 ml (43 mmol) of iodoethane are added and the mixture is then brought back to ambient temperature and stirred for an entire weekend. It is then poured into a saturated solution of ammonium chloride and extracted twice with diethyl ether. The organic phase is washed with water and then dried and concentrated to dryness. The residue is purified by flash chromatography (95/5 heptane/EtOAc). 3.6 g of (4-bromo-2-tert-butylphenyl)diethylamine are obtained in the form of a yellow oil (yield=63%).

後処理

  1. customis then brought back to ambient temperature
  2. extractionextracted twice with diethyl ether
  3. washThe organic phase is washed with water
  4. customdried
  5. concentrationconcentrated to dryness
  6. customThe residue is purified by flash chromatography (95/5 heptane/EtOAc)

出典と根拠

ORDレコード
ord-e418f9606d294fcda0bf55addd72f14d
出典データセット
uspto-grants-2012_04
特許番号
US08163952B2

反応ノート

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