Ammonium Chloride → HCID 59750758, compound

Participants

Reaction Steps

Under an argon atmosphere and at −78° C., n-butyl lithium (a 1.57M hexane solution, 7.01 ml) was added dropwise to a dimethoxyethane solution (50 ml) of the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (3.03 g, 10.0 mmol) obtained in Example 5. The temperature of the reaction mixture was raised to room temperature. Then, the reaction mixture was cooled to −78° C. After the addition of t-butyl bromoacetate (1.48 ml, 10.0 mmol), the resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was added with a saturated aqueous ammonium chloride solution, followed by extraction with diethyl ether. The extracts were combined, washed successively with water and brine, dried over MgSO4, and then distilled to remove the solvent. The residue thus obtained was subjected to chromatography on a short silica gel column (hexane-ethyl acetate 3:1). The solid thus obtained was recrystallized from hexane, whereby the title compound (3.30 g, 79%) was obtained as a colorless solid.

Provenance & Evidence