HCID 23053926, compound → HCID 22998939, compound

Participants

Reaction Steps

A suspension of 2-(3-bromophenoxymethyl)benzoate (35 g, 0.11 mole) in 100 mL of trifluoroacetic anhydride containing 20 drops of boron trifluoride-ether complex was refluxed for 4 hours. The mixture was poured into ice-water and then extracted with diethyl ether. Concentration of ether solution under reduced pressure and chromatography of the residue on a silica gel column (Waters Associates, Prep 500) with hexane/methylene chloride (70:30) gave the pure product (14 g). m.p. 110°-112° C. pmr (CDCL3) δ: 8.10 (d, J=9.1 Hz, 1H, H1), 7.90 (dd, J=1.4, 7.6 Hz, 1H, H10) 7.57 (dt, J=1.4, 7.4, 7.4 Hz, 1H H8), 7.48 (dt, J=1.4, 7.6, 7.6 Hz, 1H, H9), 7.36 (dd, J=1.3, 7.3 Hz, 1H, H7), 7.27 (d, J=1.8 Hz, 1H, H4), 7.24 (dd, J=1.8, 9.1 Hz, 1H, H2), 5.18 (s, 2H, ArCH2O).

Provenance & Evidence