2-Bromoethanol → 3-(2-Bromoethoxy)thiophene

5.00 g of 3-methoxythiophene (Aldrich) was solubilized with 11.00 g of 2-bromoethanol in 20 mL of toluene, then 2.00 g of NaHSO4 was added in one portion. The mixture was heated and methanol was distilled off. The solution was cooled and washed with water and diethylether. The organic phase was dried with magnesium sulfate. After evaporation, a brown liquid was obtained which was purified by column chromatography on silica gel using a mixture of CCl4 and CHCl3 (9:1) as the eluent. An oil was recovered which was further purified by recrystallization in methanol. White crystals were then obtained with a yield of 67%. M.P.=46° C.

1. temperatureThe mixture was heated
2. distillationmethanol was distilled off
3. temperatureThe solution was cooled
4. washwashed with water and diethylether
5. dry with materialThe organic phase was dried with magnesium sulfate
6. customAfter evaporation
7. customa brown liquid was obtained which
8. customwas purified by column chromatography on silica gel using
9. additiona mixture of CCl4 and CHCl3 (9:1) as the eluent
10. customAn oil was recovered which
11. customwas further purified by recrystallization in methanol
12. customWhite crystals were then obtained with a yield of 67%

ORD record

ord-d0c4bcf045244f7fa4dce6c1d32e3897

Source dataset

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06051679