반응 #569261

반응 방정식

3-benzyloxyphenol

N,N-diisopropylethylamine

2-chlorobenzenesulfonyl chloride

→

title compound

수율 95.2%

2-Chlorobenzenesulfonic acid 3-benzyloxyphenyl ester

수율 95.2%

용매

methylene chlorine

methylene chloride

반응 조건

후처리

1. 1
   세척washed sequentially with saturated NaHCO3 (2×50 mL) and brine (2×50 mL)
2. 2
   건조dried over Na2SO4
3. 3
   농축concentrated in vacuo
4. 4
   기타The residue was purified by flash column chromatography (1:1 hexane:methylene chloride)

실험 절차

To a solution of 3-benzyloxyphenol (2.97 g, 15 mmol), as prepared in the preceding step, in methylene chlorine (50 mL) at 0° C., was added N,N-diisopropylethylamine (2 mL) and 2-chlorobenzenesulfonyl chloride (3.27 g, 15.5 mmol). The reaction mixture was stirred at 0° C. for 2 h and at room temperature for 2 h. The reaction mixture was diluted with methylene chloride (200 mL), washed sequentially with saturated NaHCO3 (2×50 mL) and brine (2×50 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography (1:1 hexane:methylene chloride) to give the title compound as a colorless liquid (5.35 g, 95%). 1H-NMR (300 MHz, CDCl3) δ 4.97 (s, 2H), 6.71 (dd, 1H), 6.78 (t, 1H), 6.85 (dd, 1H), 7.17 (t, 1H), 7.37 (m, 5H) 7.58 (m, 2H), 7.91 (dd, 1H).

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