Application of 955959-84-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 955959-84-9 name is 4-(4-Bromophenyl)dibenzo[b,d]furan, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
A solution of dibenzofuran-4-boronic acid (1.0 g, 4.7 mmol) in ethanol (10 ML) was added to a stirred solution of 1- bromo-4-iodobenzene (1.33 g, 4.7 mmol) and tetrakis- (triphenylphosphine) palladium (0) (271 mg, 5 MOLpercent) in toluene (40 mL). 2N sodium carbonate (4.7 mL, 9.4 mmol) was added and the reaction was heated to 90°C (oil bath temp. ) for 2-3 hrs until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and diethyl ether. The phases were separated, the aqueous phase being further extracted with diethyl ether (2 x 20 mL). The combined extract was washed with water and brine. The ethereal solution was dried over anhydrous MGS04, filtered and concentrated in vacuo to yield 4- (4-BROMOPHENYL)-DIBENZOFURAN as a yellow solid, which was used immediately without further purification. A solution of 4-FORMYLPHENYLBORONIC acid (0.9 g, 5.64 mmol) in ethanol (10 mL) was added to a stirred solution of the crude 4- (4-BROMOPHENYL)-DIBENZOFURAN (from the previous reaction) in toluene (40 mL). tetrakis- (Triphenylphosphine) palladium (0) (270 mg, 5 molpercent) and 2N sodium carbonate (4.7 mL, 9.4 mmol) were added and the reaction was heated to 100°C (oil bath temp. ) for 2-3 hrs until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The phases were separated, the aqueous phase being further extracted with ethyl acetate (2 x 20 mL). The combined extract was washed with 0.5 N hydrochloric acid, water and brine and then dried over anhydrous MGS04, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 10-20percent ethyl acetate in hexane as eluent, afforded the title compound has a white solid (1.51g).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(4-Bromophenyl)dibenzo[b,d]furan, and friends who are interested can also refer to it.
Reference:
Patent; THE INSTITUTE OF PHARMACEUTICAL DISCOVERY, LLC; WO2004/99170; (2004); A2;,
Bromide – Wikipedia,
bromide – Wiktionary