Reaction #2358525

Reaction equation

tert-butyl 2-[3-fluoro-5-(methylsulfonyl)phenoxy]ethyl-carbamate

HCl

NaOH

→

title compound

Yield 78.6%

2-[3-fluoro-5-(methylsulfonyl)phenoxy]ethanamine

Yield 78.6%

Solvents

EtOH

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate (2×100 ml)
2. 2
   WashThe combined organic phase was washed with brine (75 ml)
3. 3
   Dryingdried (Na2SO4)
4. 4
   Otherevaporated

Procedure

A mixture of tert-butyl 2-[3-fluoro-5-(methylsulfonyl)phenoxy]ethyl-carbamate (1.4 g, 4.2 mmol) in EtOH (18 ml) was added HCl (1.25 M in EtOH, 6 ml). The mixture was stirred at ambient temperature for 20 h. The aqueous phase was made basic by addition of aqueous NaOH (1 M, 50 ml) and extracted with ethyl acetate (2×100 ml). The combined organic phase was washed with brine (75 ml), dried (Na2SO4) and evaporated to yield the title compound (0.77 g, 77%). MS m/z (relative intensity, 70 eV 298 (M+, 18), 296 (M+, 18), 109 (bp), 107 (99), 82 (15).

Source