Water → HCID 86728169, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromo-1,2-dichlorobenzene (0.9 mL, 7 mmol), (E)-tert-butyldimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-enyloxy)silane (3.0 mL, 8.3 mmol), KF (1.2 g, 21 mmol), Pd(OAc)2 (0.16 g, 0.70 mmol), and 2-(di-tert-butylphosphino)biphenyl (0.41 g, 1.4 mmol) were combined in a 20 mL microwave tube and the tube was sealed, evacuated and backfilled with argon. Degassed THF (20 mL) and H2O (0.25 mL, 14 mmol) were added under argon, and the mixture was heated to 150° C. for 60 min using microwave irradiation. The reaction mixture was cooled to rt and stirred for 3 days. The reaction mixture was diluted with ethyl acetate (200 mL). The organic layer was washed with water (200 mL) and brine (100 ml), dried over Na2SO4 and concentrated to give a black oil that was stored overnight at −20° C. The crude product was dissolved in hexanes/DCM and purified by silica gel chromatography (100% hexanes for 10 min, 0-3% ethyl acetate in hexanes over 20 min) to obtain 2.0 g (67% yield) of Intermediate 2A. HPLC/MS (Method C) RT=4.80 min, [M-C6H16OSi]+ 199.1.

Provenance & Evidence