Sodium Hydroxide → 1-Fluoro-4-(propylsulfonyl)benzene

A cooled (0° C.) solution of 4-fluorothiophenol (Merck Kgaa; 2.00 g; 15.6 mmol) in MeOH (40 ml) was treated with a 5 N solution of NaOH in water (3.28 ml) and 1-iodopropane (1.67 ml; 17.2 mmol). The reaction mixture was stirred at RT for 1 hour, the mixture was concentrated under reduced pressure, the residue taken up in EtOAc and washed with brine, dried on MgSO4, filtered and concentrated under reduced pressure. The intermediate thus obtained was dissolved in DCM (50 ml) and treated with 3-chloroperbenzoic acid (8.46 g; 34.33 mmol) and stirred at RT for 3 hours. The solvent was removed under reduced pressure, the residue taken up in EtOAc and washed with brine, dried on MgSO4, filtered and concentrated under reduced pressure to afford the title compound (2.75 g, 87%).

1. concentrationthe mixture was concentrated under reduced pressure
2. washwashed with brine
3. customdried on MgSO4
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customThe intermediate thus obtained
7. stirringstirred at RT for 3 hours
8. customThe solvent was removed under reduced pressure
9. washwashed with brine
10. customdried on MgSO4
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure

ORD record

ord-0f9931167aee42fe980c388bf99bc466

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273769B2