Dimethylformamide → HCID 20071127, compound

Participants

Reaction Conditions

Reaction Steps

Charge an oven dried, argon flushed 25-mL 2-necked round bottomed flask equipped with a stirring bar and reflux condenser with 2-t-butyldimethylsilyloxy-3,4-dihydronaphthalene (0.5007 grams, 1.9224 mmoles) and tetra-n-butylammonium fluoride (2.3 mL, 2.30 mmoles, 1 M in tetrahydrofuran), stir for a few minutes and then add 4-bromo-2-methoxy-2-chlorobenzene (0.4287 grams, 1.9356 mmoles), dichlorobis(tri-o-tolyl-phosphine)palladium (0.0154 grams, 0.0196 mmoles) and 5 mL dimethylformamide. Heat the reaction mixture for 18 hours (oil bath temperature about 90° C.), cool to RT and add 5 mL water and 10 mL t-butylmethyl ether. Separate the layers, extract the aqueous layers with 3×5 mL t-butylmethyl ether, wash the combined organic layers with water and saturated salt solution, dry over magnesium sulfate and concentrate using a Buchi rotavapor to yield the product.

Provenance & Evidence