Hydrochloric Acid → 2-Bromo-3-ethylbenzenamine

HRID 2203215Notes

Reaction equation

HRID 2203215 reaction equation
[Br:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:11][CH3:12].Cl>CCO>[Br:1][C:2]1[C:3]([CH2:11][CH3:12])=[CH:4][CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 215318672-Bromo-1-ethyl-3-nitrobenzene

Product 1

HCID 235006992-Bromo-3-ethylbenzenamineYield 81.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2-bromo-1-ethyl-3-nitrobenzene (9.2 g, 40 mmol) in EtOH (100 mL) in concentrated hydrochloric acid (0.17 mL, 2 mmol) was refluxed for 2 hours. The mixture was subsequently purified by column chromatography, eluting with petroleum ether to give the title compound as a red oil (6.5 g, 81%). 1H NMR (400 MHz, CDCl3) δ 7.03 (1H, dd, J=7.6, 8.0 Hz), 6.64-6.62 (2H, m), 2.73 (2H, q, J=7.6 Hz), 1.22 (3H, t, J=7.6 Hz).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customThe mixture was subsequently purified by column chromatography
  3. washeluting with petroleum ether

Sources & evidence

ORD record
ord-6f13203b8cc64e92b3d6fac71ab3efdc
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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