2-Bromothiophene → 2-Phenylthiophene

An oven dried Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol %), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol %), phenylboron dihydroxide (183 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 2-bromothiophene (0.097 mL, 1.0 mmol) were added through a rubber septum. The reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ethyl acetate (30 mL) and poured into a separatory funnel. The mixture was washed with 2.0M NaOH (20 mL). The organic layer was washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 159 mg (99%) of the title compound.

1. customAn oven dried Schlenk tube
2. customwas evacuated
3. customThe tube was evacuated
4. additionwere added through a rubber septum
5. customhad been completely consumed
6. additionThe reaction mixture was then diluted with ethyl acetate (30 mL)
7. additionpoured into a separatory funnel
8. washThe mixture was washed with 2.0M NaOH (20 mL)
9. washThe organic layer was washed with brine (20 mL)
10. dry with materialdried over anhydrous magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated
13. customThe crude material was purified by flash chromatography on silica gel

ORD record

ord-14ada9c0eea5403da78b931fbd6caf62

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07026498B2