1-Bromo-3-methylbutane → Thiophene, 2-isopentyl-

Temperature

0 °C

Isopentyl bromide (Aldrich, 8 g, 53mmol) was added to 53 mL of an ice-cooled solution of lithiothiophene (1.0M in THF, 53 mmol). The reaction was stirred at 0° C. for 2 hours, at room temperature for 16 hours, and poured into water, then the mixture was extracted with hexane. The organic layer was dried and concentrated, and the residue was purified by column chromatography on silica gel, eluting with hexane, to give 7.2 g (88% yield) of the title compound as a colorless oil. NMR (CDCl3) δ:7.10 (dd, J=1, 6 Hz, 1H), 6.90 (dd, J=4, 6 Hz, 1H), 6.78 (dd, J=1, 4 Hz, 1H), 2.84 (t, J=8 Hz, 2H), 1.7-1.5 (m, 3H), 0.94 (d, J=6 Hz, 6H).

1. extractionthe mixture was extracted with hexane
2. customThe organic layer was dried
3. concentrationconcentrated
4. customthe residue was purified by column chromatography on silica gel
5. washeluting with hexane

ORD record

ord-524b9e03480a4f4b83c07433c4943f12

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05597832