Triethylamine → Methyl 4-bromo-1-benzothiophene-2-carboxylate

Temperature

100 °C

Methyl thioglycolate (42.35 g) was added under nitrogen at 80° C. to a solution of triethylamine (109 ml) in dimethylformamide (290 ml), the mixture was stirred at 100° C. for 15 minutes, then a solution of 2-bromo-6-fluorobenzaldehyde (81.35 g; prepared in a manner similar to that described above) in dimethylformamide (70 ml) was added. The mixture was stirred at 130° C. for 5 hours, then it was cooled to ambient temperature and poured into ice-water (3000 ml). The resulting solid was collected by filtration, washed with water (2×250 ml) and dried in air to give methyl 4-bromobenzo[b]thiophene-2-carboxylate (101 g) as a yellow solid which was used without further purification.

1. customprepared in a manner similar to
2. additionwas added
3. stirringThe mixture was stirred at 130° C. for 5 hours
4. temperatureit was cooled to ambient temperature
5. filtrationThe resulting solid was collected by filtration
6. washwashed with water (2×250 ml)
7. customdried in air

ORD record

ord-d87411a842bc4219998c57a308c50d41

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06900216B2