Pyridine → 4-(2-Chloro-ethanesulfonyl)-phenol

Participants

Reaction Steps

A solution of 6.81 g crude 4-(2-hydroxy-ethansulfonyl)-phenol in 35 ml CH2Cl2 was treated at room temperature with 5.3 ml (65.9 mmol) pyridine. To the reaction mixture was added at 0° C. dropwise over 15 min a solution of 4.2 ml (57.1 mmol) thionyl chloride in 10 ml CH2Cl2. After 65 h at room temperature the reaction mixture was treated with 35 ml brine, extracted and the organic phases were washed twice with total 100 ml aqueous half saturated NaCl solution. The combined organic phases were dried over Na2SO4 and the solvent was removed under reduced pressure to yield 6.77 g crude product. The crude product was dissolved in 2.5 ml CH2Cl2 and 25 ml toluene, stirred 24 h at 50° C.) 24 h at room temperature and 48 h at 0° C. The so formed suspension was filtered to yield 5.44 g (86.5% over 2 steps) product as white crystals.

Provenance & Evidence