2-Bromothiophene → HCID 22677667, compound

To a mixture of magnesium (0.25 g, 10.58 mmol) in anhydrous THF (5.3 mL) was added 2-bromothiophene (1.73 g, 10.58 mmol) dropwise. The mixture was heated at reflux under argon for 0.5 h. An additional 0.35 g of 2-bromothiophene was added to consume the remaining magnesium. The reaction mixture was heated for additional 1.5 h to afford a solution which was transferred to a mixture of 1-bromo-2-fluoro-4-methylbenzene (2.0 g, 10.58 mmol), Pd(PPh3)4 (0.61 g, 0.53 mmol), and THF (23.5 mL). The resulting mixture was heated under argon for 3 h. The reaction was allowed to cool to rt and quenched with water. The mixture was extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated down under reduced pressure. The crude product was purified by flash column chromatography eluting with hexane to afford a colorless liquid (1.46 g, 72%): 1H NMR (CDCl3), δ 7.48-7.02 (m, 6H), 2.36 (s, 3H), GC/MS m/z 192 (M+, 100).

1. temperatureThe mixture was heated
2. temperatureat reflux under argon for 0.5 h
3. customto consume the remaining magnesium
4. temperatureThe reaction mixture was heated for additional 1.5 h
5. customto afford a solution which
6. temperatureThe resulting mixture was heated under argon for 3 h
7. customquenched with water
8. extractionThe mixture was extracted with CH2Cl2
9. dry with materialThe organic layer was dried over MgSO4
10. concentrationconcentrated down under reduced pressure
11. customThe crude product was purified by flash column chromatography
12. washeluting with hexane

ORD record

ord-ebcc73d8fce74f099ade257b946cc8f4

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06784167B2