Hydrochloric Acid → 1-Bromo-2-chloro-3-methylbenzene

HRID 1042354Notes

Reaction equation

HRID 1042354 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6](N)=[C:5]([CH3:10])[C:4]=1[Cl:11].N([O-])=O.[Na+]>CCO>[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:10])[C:4]=1[Cl:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 71719114-Bromo-3-chloro-2-methylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 133481341-Bromo-2-chloro-3-methylbenzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Concentrated HCl was added to a solution of 4-bromo-3-chloro-2-methyl-phenylamine (4.98 g, 22.60 mmol) in EtOH. NaNO2 (3.00 g, 43.50 mmol) was added and the resulting mixture was heated to 70° C. for 2 hours. Ethanol was distilled off and the residue was purified by column chromatography using hexanes as the eluant to afford the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ 2.43 (s, 3H), 7.01 (t, J=7.91 Hz, 1H), 7.18 (d, J=7.62 Hz, 1H), 7.47 (d, J=7.91 Hz, 1H).

Workup

  1. distillationEthanol was distilled off
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c3199ebd740742edacdf4e2861858c08
Source dataset
uspto-grants-2013_10
Patent number
US08557853B2

Reaction notes

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