Dichloromethane → 3-Bromo-4-ethylaniline

HRID 2252837Notes

Reaction equation

HRID 2252837 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:10]([O-])=O)[CH:5]=[CH:6][C:7]=1[CH2:8][CH3:9].C(Cl)Cl>C(O)C.[Ni]>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[CH2:8][CH3:9])[NH2:10]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 223455942-Bromo-1-ethyl-4-nitrobenzene

Product 1

HCID 223456173-Bromo-4-ethylaniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Hydrogenation of 4.45 g (19 mmol) of 3-bromo-4-ethyl-nitrobenzene (for preparation see Macromolecules 1995, 28, 5618) in 100 ml of ethanol in the presence of 1 g of Raney nickel, followed by filtration, concentration by evaporation and chromatography (SiO2; methylenechloride), yields 3-bromo-4-ethyl-aniline; 1H NMR (CDCl3) δ 6.94 (d, 1H), 6.82 (s, 1H), 6.50 (d, 1H), 3.50 (s, H2N), 2.57 (q, 2H), 1.10 (t, 3H).

Sources & evidence

ORD record
ord-756131f0ce674fb38e16469eab0ac0d7
Source dataset
uspto-grants-2008_01
Patent number
US07323474B2

Reaction notes

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