Dimethyl Sulfoxide → (2,2-Difluoro-1,3-dioxaindan-5-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole (117.6 g, crude from last step) and NaCN (84 g, 1.7 mmol) in DMSO (800 mL) was stirred for 2 h at 25° C. The reaction, mixture was poured into ice and extracted with EtOAc (500 mL×3). The combined organic layers were dried with anhydrous Na2SO4 and concentrated in vacuo to give crude product which was purified by column chromatography (P.E./EtOAc 10:1) to give (2,2-difluorobenzo[d][1,3]dioxol-5-yl)methanol (77.8 g, 66%), 1H NMR (300 MHz , CDCl3) δ 7.06-7.07 (m, 3H), 3.75 (s, 2H).

Provenance & Evidence