Reaction #9342

Reaction equation

diisobutylamine

Diisobutylamine

6-hydroxy-7-propyl-3-trifluoromethylbenzisoxazole

sodium bisulfite

benzisoxazole

sulfuryl chloride

→

title compound

5-Chloro-6-hydroxy-7-propyl-3-trifluoromethyl-1,2-benzisoxazole

Solvents

toluene

ethyl ether

Conditions

Workup

1. 1
   Otherresults in a suspension which
2. 2
   OtherThe phases were separated
3. 3
   WashThe ether phase was washed with brine
4. 4
   Dryingdried over Na2SO4
5. 5
   OtherThe solvent was evaporated in vac
6. 6
   Otherto give an orange solid which
7. 7
   Otherwas purified by chromatography on silica gel eluting with acetone:hexane (2:98)

Procedure

Diisobutylamine (0.8 ml, 0.10 eq) and 6-hydroxy-7-propyl-3-trifluoromethylbenzisoxazole (11 gm, 1.0 eq) were dissolved in toluene (275 ml) at room temperature. Slow addition of sulfuryl chloride (4.20 ml, 1.15 eq) results in a suspension which was stirred overnight. Additional diisobutylamine (total 1.6 ml, 0.4 eq) was added in four equal portions over 24 hr until no further starting benzisoxazole was detected by analytical TLC. The reaction mixture was poured into saturated sodium bisulfite (500 ml) and ethyl ether (700 ml). The phases were separated. The ether phase was washed with brine and dried over Na2SO4. The solvent was evaporated in vac to give an orange solid which was purified by chromatography on silica gel eluting with acetone:hexane (2:98) to give the title compound.

Source