Chlorosuccinimide → 4-Chloro-2-methyl-3-nitrophenol
Reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[Cl:12]N1C(=O)CCC1=O.FC(F)(F)S(O)(=O)=O>C(#N)C.C(OCC)C>[Cl:12][C:6]1[CH:5]=[CH:4][C:3]([OH:11])=[C:2]([CH3:1])[C:7]=1[N+:8]([O-:10])=[O:9]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 75 °C
Procedure
2-Methyl-3-nitrophenol (25.5 g), N-chlorosuccinimide (44.5 g), and trifluormethanesulfonic acid (50.0 g) were combined in dry acetonitrile (500 mL) and allowed to stir under an atmosphere of nitrogen at 75° C. for 1.5 hr. The reaction mixture was cooled to room temperature, diluted with ethyl ether (650 mL), washed with water, 10% sodium bisulfite solution, water, and finally saturated sodium chloride solution. Evaporation of the solvent afforded a crude material which was flash chromatographed on silica and eluted with acetone:hexane (1:9) to afford 16.8 g as a yellow solid.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- washwashed with water, 10% sodium bisulfite solution, water, and finally saturated sodium chloride solution
- customEvaporation of the solvent
Sources & evidence
- ORD record
- ord-254b63ae05a547bdbb40d5d13db1ee86
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05952362
Reaction notes
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