Acetic Acid → 1-(3-Fluoro-4-(methylsulfonyl)phenyl)propan-2-one

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence