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

HRID 1158147Notes

Reaction equation

HRID 1158147 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.[CH2:15](I)[CH3:16].[Cl-].[NH4+].O1CC[CH2:22][CH2:21]1>CS(C)=O>[Br:3][C:4]1[CH:10]=[CH:9][C:7]([N:8]([CH2:15][CH3:16])[CH2:21][CH3:22])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1

Participants

7

Reactant 5

HCID 6340IodoethaneHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 119590004-bromo-2-tert-butylphenylamine

Product 1

HCID 666719634-Bromo-2-(1,1-dimethylethyl)-N,N-diethylbenzenamineYield 91%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6.9 g (0.17 mol) of sodium hydride are suspended in 200 mL of tetrahydrofuran. 13 g (57 mmol) of 4-bromo-2-tert-butylaniline are added, along with 200 mL of dimethyl sulfoxide, added slowly. The mixture turns blue and, after 30 minutes, 13 mL (0.17 mol) of ethyl iodide are added and the reaction medium, which has turned white, is stirred at room temperature for 13 hours. The reaction medium is then poured into saturated ammonium chloride solution and extracted with ethyl acetate, and the organic phase is then washed twice with water. It is dried and then concentrated to dryness. The residue is purified by chromatography on silica gel (eluent: 90/10 heptane/ethyl acetate). 14.8 g of (4-bromo-2-tert-butylphenyl)diethylamine are obtained (yield=91%) in the form of a yellow oil.

Workup

  1. additionadded slowly
  2. extractionextracted with ethyl acetate
  3. washthe organic phase is then washed twice with water
  4. customIt is dried
  5. concentrationconcentrated to dryness
  6. customThe residue is purified by chromatography on silica gel (eluent: 90/10 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-a839151c14c7491892e272a0e0e70ade
Source dataset
uspto-grants-2010_10
Patent number
US07807708B2

Reaction notes

Loading…