Benzothiophene, 4,5,6,7-tetrahydro- → 2-Bromo-4,5,6,7-tetrahydro-1-benzothiophene

Temperature

0 °C

4,5,6,7-Tetrahydrobenzo[b]thiophene (0.252 g, 1.79 mmol) was dissolved in chloroform (10 mL), cooled to 0° C. and N-bromosuccinimide (0.334 g, 1.88 mmol) was added. The reaction mixture was stirred at 0° C. for 1 h then at ambient temperature for 1.75 h and then heated at 40° C. for a further 4 h. The reaction mixture was cooled to room temperature, concentrated in vacuo and the residue diluted with water and extracted with diethyl ether (4×10 mL). The combined organic phase was washed with water and brine, dried over sodium sulfate, filtered and evaporated to afford the title compound (0.35 g, 88%) as a brown oil. NMR (CDCl3, 300 MHz): 6.69 (s, 1H), 2.73-2.59 (m, 2H), 2.58-2.49 (m, 2H), 1.88-1.70 (m, 4H).

1. waitat ambient temperature for 1.75 h
2. temperatureheated at 40° C. for a further 4 h
3. temperatureThe reaction mixture was cooled to room temperature
4. concentrationconcentrated in vacuo
5. additionthe residue diluted with water
6. extractionextracted with diethyl ether (4×10 mL)
7. washThe combined organic phase was washed with water and brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. customevaporated

ORD record

ord-ded7fc365ff54aa893cffb73948b411e

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216980B2