Ethanol → Biphenyl

Resin-bound aryl silane intermediate 4-Scheme 1 (2 g) was suspended in toluene (15 mL) and allowed to swell for 30 minutes. To this was added tetrkistriphenylphosphine (275 mg, 0.25 mmol), phenylboronic acid (500 mg, 4.1 mmol), ethanol (2 mL), sodium carbonate, aq (2 mL, 2M), all of which was heated in an oil bath maintained at 90° for 16 h. The reaction mixture was cooled, filtered washed with methanol, water, methylene chloride and methanol to give a black solid which was taken for the next step. A portion of the above resin (1 g) was treated with trifluoroacetic acid (3 mL) and stored at room temperature for 24 h. Methylene chloride (10 mL) was added and filtered, washed with methylene chloride. Removal of solvents gave a slight brown oil which was triturated with hexane (50 mL). Evaporation of the hexanes yielded biphenyl (78 mg) which was come with an authentic sample.

1. temperatureall of which was heated in an oil bath
2. temperaturemaintained at 90° for 16 h
3. temperatureThe reaction mixture was cooled
4. filtrationfiltered
5. washwashed with methanol, water, methylene chloride and methanol
6. customto give a black solid which
7. waitstored at room temperature for 24 h
8. filtrationfiltered
9. washwashed with methylene chloride
10. customRemoval of solvents
11. customgave a slight brown oil which
12. customwas triturated with hexane (50 mL)
13. customEvaporation of the hexanes

ORD record

ord-1a1b42844b84480f8ecc572a75b422ed

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05773512