Dichloromethane → HCID 18687729, compound

Participants

Reaction Steps

A stirred 3-methoxyphenoxathiin (3.00, 13.03 mmol) 25 ml CH2Cl2 was cooled to -70° C. under N2 and BBr3 (45.6 ml, 45.6 mmol, 1.0 M in CH2Cl2) was added dropwise over 1 h. The resulting bright, blue, heterogeneous mixture was allowed to warm to room temperature and stirred overnight. After 21 h the yellow homogeneous reaction is cooled to -60° C. and poured onto 300 mL MeOH at -60° C. After warming to room temperature the solution was concentrated in vacuo to a dark yellow oil which was purified by column chromatography (CH2Cl2 /hexane, gradient elution, 50:50 to 100:00) to give 2.59 g (91%) 3-phenoxathiinol as a white solid. TLC (CH2Cl2 /hexane 50:50) Rf =0.14; HPLC (Tr =14.2), 1H-NMR (CDCl3) δ 4.78 (s, 1H, --OH), δ 6.52 (d, J=8 Hz, 1H, C2 --H), δ 6.56 (s, 1H, C4 --H), δ 6.92-7.14 (m, 5H); MS m/z (relative intensity) 217 (MH+, 100).

Provenance & Evidence