Reaktion #569261

Reaktionsgleichung

3-benzyloxyphenol

N,N-diisopropylethylamine

2-chlorobenzenesulfonyl chloride

→

title compound

Ausbeute 95.2%

2-Chlorobenzenesulfonic acid 3-benzyloxyphenyl ester

Ausbeute 95.2%

Lösungsmittel

methylene chlorine

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed sequentially with saturated NaHCO3 (2×50 mL) and brine (2×50 mL)
2. 2
   Trocknendried over Na2SO4
3. 3
   Einengenconcentrated in vacuo
4. 4
   SonstigeThe residue was purified by flash column chromatography (1:1 hexane:methylene chloride)

Vorschrift

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).

Quelle