Acetic Acid → 1-(3-Fluoro-4-(methylsulfonyl)phenyl)propan-2-one
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]=[C:9]([N+]([O-])=O)[CH3:10])[CH:5]=[CH:4][C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15].C(O)(=[O:20])C>[Fe]>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9](=[O:20])[CH3:10])[CH:5]=[CH:4][C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
Freshly prepared 2-fluoro-1-methanesulfonyl-4-(2-nitro-propenyl)-benzene (Example 68b) (20 g, 77 mmol) in glacial acetic acid (150 ml) is added slowly in 15×10 ml portions to a stirred slurry of iron powder (46 g, 833 mmol) in glacial acetic acid (150 ml) at 60° C. The reaction mixture is heated at 100° C. for an additional 2 hours, allowed to cool to room temperature and poured on to ice water (600 ml). The mixture is filtered through celite to remove iron residues, washing with dichloromethane (300 ml). The organic layer is removed and the aqueous solution is extracted with more DCM (3×200 ml). The combined organic extracts are dried (MgSO4), filtered and concentrated to a red solution. The titled product crystallises from this solution on standing.
Workup
- temperatureto cool to room temperature
- filtrationThe mixture is filtered through celite
- customto remove iron residues
- washwashing with dichloromethane (300 ml)
- customThe organic layer is removed
- extractionthe aqueous solution is extracted with more DCM (3×200 ml)
- dry with materialThe combined organic extracts are dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated to a red solution
- customThe titled product crystallises from this solution on standing
Sources & evidence
- ORD record
- ord-3623579ccba74c31a457b3b0071a74b2
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08017608B2
Reaction notes
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