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

HRID 1698394노트

반응식

HRID 1698394 반응식
[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

참가 물질

6

반응물 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 66671970HCID 66671970, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-e418f9606d294fcda0bf55addd72f14d
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163952B2

반응 노트

불러오는 중…