Sodium Carbonate → 5-Chloro-1-benzothiophene-3-carbaldehyde

A stirred mixture of 5-chloro-3-methylbenzothiophene (39 g, 0.214 mole, (D22)) and recrystallized N-bromosuccinimide (77 g, 0.432 mole) in carbon tetrachloride (700 ml) was illuminated with a 100 W lamp, while heating at reflux temperature for 4 hours. The reaction mixture was allowed to cool, the solid was filtered off and the filtrate was evaporated to dryness to leave a yellow oil. This residue was treated with 10% sodium carbonate solution (450 ml) and heated under rflux, with vigorous stirring, for 5 hours. The mixture was allowed to cool and extracted with chloroform (3×200 ml). The organic solution was washed with brine (2×200 ml), dried (MgSO4) and evaporated to dryness to give the title compound as a red solid (37 g, 88%).

1. customwas illuminated with a 100 W lamp
2. temperaturewhile heating
3. temperatureat reflux temperature for 4 hours
4. temperatureto cool
5. filtrationthe solid was filtered off
6. customthe filtrate was evaporated to dryness
7. customto leave a yellow oil
8. temperatureheated under rflux, with vigorous stirring, for 5 hours
9. temperatureto cool
10. extractionextracted with chloroform (3×200 ml)
11. washThe organic solution was washed with brine (2×200 ml)
12. dry with materialdried (MgSO4)
13. customevaporated to dryness

ORD record

ord-288a68df31c7449f871971ce70bb66f4

Source dataset

uspto-grants-1985_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04548948