Isoamyl Nitrite → 1,5-Dibromo-2-chloro-3-fluorobenzene
Reaction equation
[Br:1][C:2]1[C:7]([Cl:8])=[C:6]([F:9])[CH:5]=[C:4]([Br:10])[C:3]=1N.C(ON=O)CC(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([Br:10])[CH:5]=[C:6]([F:9])[C:7]=1[Cl:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A solution of 2,6-dibromo-3-chloro-4-fluoro-phenylamine (1a, 4.85 g, 16 mmol, 1 eq.) in DMF (20 mL) was added to a solution of isoamylnitrite (3.46 mL, 25.6 mmol, 1.6 eq.) in DMF (12 mL) at 70° C. The mixture was heated at 70° C. for 3 h before it was cooled to room temperature, quenched with 1 N NaOH aqueous solution (150 mL), and extracted with EtOAc (200 mL). The EtOAc extract was washed with brine (100 mL×2), dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (heptane) to give desired product 2a as colorless oil (3.70 g, 80%).