Hydrochloric Acid → 3-Bromo-5-fluoro-4-methylaniline

HRID 1417530Notes

Reaction equation

HRID 1417530 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:10]([O-])=O)[CH:5]=[C:6]([F:9])[C:7]=1[CH3:8].Cl>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:9])[C:7]=1[CH3:8])[NH2:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 542079842-Bromo-6-fluoro-4-nitrotoluene

Product 1

HCID 534842563-Bromo-5-fluoro-4-methylanilineYield 106.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 3-bromo-5-fluoro-4-methylnitrobenzene (1.4 gm, 6.0 mmol) in ethanol (100%, 25 mL) was added (c) HCl (7.0 mL) and stannous chloride dihydrate (4.1 gm, 18 mmol). The solution was stirred at room temperature for 16 hr and then concentrated in vacuo. The residue was diluted with water, made basic with 2N NaOH and extracted twice with ether. The ether layers were each washed with brine, dried over sodium sulfate, combined and evaporated to give 1.3 gm of crude title compound as an oil. NMR (CDCl3): δ 2.17 (d, 3H, J=3 Hz), 6.31 (dd, 1H, J=2.2 and 11 Hz), 6.67 (dd, 1H, J=1.8 and 2.2 Hz).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted twice with ether
  4. washeach washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-e9a8011395d749caa375706f5ffad7c1
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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