Hydrochloric Acid → 3-Bromo-5-fluoro-4-methylaniline
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
Product 1
Reagents, catalysts & solvents 1
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
- concentrationconcentrated in vacuo
- additionThe residue was diluted with water
- extractionextracted twice with ether
- washeach washed with brine
- dry with materialdried over sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-e9a8011395d749caa375706f5ffad7c1
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05877191
Reaction notes
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