Ethyl Acetate → 2-broMo-4-ethylbenzenaMine

HRID 2063542Notes

Reaction equation

HRID 2063542 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)[CH3:2].C1C(=O)N([Br:17])C(=O)C1.CCOC(C)=O>C(Cl)(Cl)Cl>[Br:17][C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[CH:8]=[CH:7][C:6]=1[NH2:9]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 115044-EthylanilineHCID 67184N-bromobutanimide

Product 1

HCID 106318572-broMo-4-ethylbenzenaMineYield 66.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Ethylphenylamine (1.00 g, 7.52 mmol, 1 equiv) was dissolved in chloroform (40 mL) and placed into an ice bath. NBS (1.34 g, 1 equiv) was then added into the solution in small portions. The mixture was warmed to room temperature and stirred for 2 hours. EtOAc (˜200 mL) was added and the mixture was filtered. The filtrate was washed with saturated aqueous K2CO3 (200 mL), saturated aqueous NaHCO3 (200 mL), and brine (200 mL), dried over magnesium sulfate and concentrated. The residue was purified by silica gel flash column chromatography using 5% to 20% EtOAc in hexanes to afford the title compound as light brown oil (1 g). MS (ES) m/z 200.0 (M+H+).

Workup

  1. customplaced into an ice bath
  2. filtrationthe mixture was filtered
  3. washThe filtrate was washed with saturated aqueous K2CO3 (200 mL), saturated aqueous NaHCO3 (200 mL), and brine (200 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-0c7be0c3b8f34c99883a1374b17f2bc3
Source dataset
uspto-grants-2012_10
Patent number
US08288373B2

Reaction notes

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