Reaction #67281

Reaction equation

[5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methanol

toluenesulfonyl chloride

DCM

DCM

→

title compound

[5-FLUORO-7-(METHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHYL 4-METHYLBENZENESULFONATE

Conditions

Workup

1. 1
   Washthe resulting mixture was washed with HCl (1 N) and brine
2. 2
   DryingThe organic phase was dried (Na2SO4)
3. 3
   Otherevaporated to dryness

Procedure

A solution of [5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (0.4 g, 1.7 mmol), toluenesulfonyl chloride (0.5 g, 2.6 mmol), TEA (0.4 ml, 2.6 mmol) and 4-DMAP (0.2 g, 1.7 mmol) in DCM (10 ml) was stirred at rt for 1 h. DCM was added and the resulting mixture was washed with HCl (1 N) and brine. The organic phase was dried (Na2SO4) and evaporated to dryness to give the title compound (0.7 g). MS m/z (rel. intensity, 70 eV) 416 (M+, 31), 244 (bp), 243 (26), 231 (19), 91 (70).

Source