Iodoethane → 4-Bromo-2-(1,1-dimethylethyl)-N,N-diethylbenzenamine

HRID 1698394Notes

Reaction equation

HRID 1698394 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 666719634-Bromo-2-(1,1-dimethylethyl)-N,N-diethylbenzenamineYield 63.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-e418f9606d294fcda0bf55addd72f14d
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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