Acetic Acid → 1-(4-Methanesulfonyl-3-trifluoromethyl-phenyl)-propan-2-one
Reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]([N+]([O-])=O)[CH3:13])=[CH:7][C:6]=1[C:17]([F:20])([F:19])[F:18])(=[O:4])=[O:3].C(O)(=[O:23])C>[Fe]>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](=[O:23])[CH3:13])=[CH:7][C:6]=1[C:17]([F:20])([F:19])[F:18])(=[O:4])=[O:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A solution of freshly prepared 1-methanesulfonyl-4-(2-nitro-propenyl)-2-trifluoromethyl-benzene (59b) (14 g, 45 mmol) in acetic acid (100 ml) is added slowly to a stirred slurry of Iron powder (27.6 g, 495 mmol) in acetic acid (100 ml) at 60° C. The reaction is then stirred at 100° C. for 2 hours then allowed to cool and poured onto ice-water (300 ml). After filtration through celite, washing with dichloromethane (500 ml), the organic extract is separated and washed with water (3×300 ml) followed by brine (500 ml). The organic extract is dried (MgSO4) and concentrated to give a red oil. Chromatography on silica, eluting with ethyl acetate-hexane, affords the titled compound as a white solid.
Workup
- temperatureto cool
- additionpoured onto ice-water (300 ml)
- filtrationAfter filtration through celite
- washwashing with dichloromethane (500 ml)
- extractionthe organic extract
- customis separated
- washwashed with water (3×300 ml)
- extractionThe organic extract
- dry with materialis dried (MgSO4)
- concentrationconcentrated
- customto give a red oil
- washChromatography on silica, eluting with ethyl acetate-hexane
Sources & evidence
- ORD record
- ord-67282e44503a458fa14bfe8f0055b058
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08017608B2
Reaction notes
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