Ammonia → 2-Phenylthiophene

Temperature

80 °C

To a solution of 2-iodothiophene (2.8 ml, 25 mmol) and palladium tetrakistriphenylphosphine (866 mg, 0.75 mmol) in toluene (50 ml) under a nitrogen atmosphere was added aqueous sodium carbonate (2M, 25 ml) followed by a solution of phenylboronic acid (3.7 mg, 30 mmol) in methanol (12.5 ml). The vigorously stirred mixture was heated at 80° C. for 6 hours and then cooled to room temperature. Aqueous sodium carbonate (2M, 125 ml), dichloromethane (250 ml) and 0.88 ammonia solution (12 ml) were added to the reaction. The two phases were separated, and the aqueous phase extracted with dichloromethane (50 ml). The combined organic phases were washed with brine (80 ml), dried (MgSO4) and evaporated in vacuo to an oil. Purification by chromatography on silica gel eluting with hexane gave the title compound as a colourless oil (1.35 g, 36%) which solidified on standing. δH (CDCl3) 7.06-7.09 (1H, m, ArH), 7.25-7.31 (3H, m, ArH), 7.35-7.39 (2H, m, ArH, 7.60-7.62 (2H, m, ArH).

1. temperaturecooled to room temperature
2. customThe two phases were separated
3. extractionthe aqueous phase extracted with dichloromethane (50 ml)
4. washThe combined organic phases were washed with brine (80 ml)
5. dry with materialdried (MgSO4)
6. customevaporated in vacuo to an oil
7. customPurification by chromatography on silica gel eluting with hexane

ORD record

ord-3f1b9a82d46446168de63c647ba4b23e

Source dataset

uspto-grants-1998_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05712285