Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 4-bromothiophenol (5.0 g, 26.4 mmol), 2,3-dichloro-1-propene (2.6 g, 23.8 mmol) and potassium carbonate (4.4 g, 31.7 mmol) in acetone (20 ml) was stirred at 55° C. for 6 hours. After cooling to room temperature, acetone was removed under vacuum and the residue was taken into water and extracted with ethyl acetate twice. The combined organic layers were washed with 1 M sodium hydroxide, water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. Diethylaniline (30 ml) was added to the residue and the resulting mixture was stirred at 185° C. for 15 hours. Ethyl acetate was added to the cooled mixture and diethylaniline was removed by washing with 1 M HCl four times. The organic layer was dried over sodium carbonate to give 5-bromo-2-methylbenzothiophene (5.3 g, 88%, 95.1% AUC GC): 1H NMR (300 MHz, CDCl3) δ 7.70 (s, 1H), 7.52 (d, J=8.7 Hz, 1H), 7.26 (dd, J=8.7, 1.8 Hz, 1H), 6.83 (s, 1H), 2.51 (s, 3H).
After cooling to room temperature
acetone was removed under vacuum
extracted with ethyl acetate twice
The combined organic layers were washed with 1 M sodium hydroxide, water and brine
dried over anhydrous sodium sulfate
filtered
concentrated under vacuum
Diethylaniline (30 ml) was added to the residue
the resulting mixture was stirred at 185° C. for 15 hours
Ethyl acetate was added to the cooled mixture and diethylaniline
was removed
by washing with 1 M HCl four times
The organic layer was dried over sodium carbonate
Source ID: ord-970ed43912ad4e12807cffb3199ccdbf