Dimethyl Ether → HCID 67608446, compound

Participants

Reaction Steps

To a 500 mL single-neck flask was added 2,3-dimethoxy-7,7-dimethyl-9-bromo-7H-benzo[C]fluoren-5-ol (10 g) prepared according to the first five steps of example 1 in US 2006/0226402 which is included herein as reference, 2-methoxyphenylboronic acid (4.3 g), sodium carbonate (5.9 g), dimethyl ether (120 mL) and water (24 mL). The mixture was purged with N2 for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.6 g) was added to the mixture. The reaction mixture was heated to reflux for 18 hours. The mixture was cooled to room temperature and poured into water (180 mL). The resulting mixture was extracted with ethyl acetate (100 mL). The top layer was dried over sodium sulfate and then condensed to lesser volume. Solid 2,3-dimethoxy-7,7-dimethyl-9-(2-methoxyphenyl)-7H-benzo[C]fluoren-5-ol (10 g) was obtained by recrystallization from solution in t-butyl methyl ether/hexanes.

Provenance & Evidence