2-Bromopropane → 1-[4-(1-Methylethyl)-2-thienyl]ethanone

1-(Thiophen-2-yl)ethanone (5.4 mL) was added to an ice cold suspension of aluminum chloride (33 g), in dry chloroform (100 mL). 2-Bromopropane (5.2 mL) was then added dropwise over 5 min. The reaction was allowed to warm to RT and stirred overnight. The dark suspension was cautiously poured onto ice and the mixture stirred for 10 min. The layers were separated and the aqueous phase extracted with DCM (100 mL). The combined organic layers were washed with sodium hydroxide solution (2M, 200 mL) and water (200 mL), dried over sodium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with 2% ethyl acetate in isohexane. The fractions containing product were combined and evaporated to give the subtitled compound as a light yellow oil. Yield 5.4 g.

1. additionThe dark suspension was cautiously poured onto ice
2. stirringthe mixture stirred for 10 min
3. customThe layers were separated
4. extractionthe aqueous phase extracted with DCM (100 mL)
5. washThe combined organic layers were washed with sodium hydroxide solution (2M, 200 mL) and water (200 mL)
6. dry with materialdried over sodium sulphate
7. filtrationfiltered
8. customevaporated
9. customThe residue was purified by silica gel chromatography
10. washeluting with 2% ethyl acetate in isohexane
11. additionThe fractions containing product
12. customevaporated

ORD record

ord-8015c02e26a0491ca61b56f491c59008

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629271B2