Phosphorus tribromide → HCID 23043711, compound

To a solution of 3-methoxybenzothiophene-2-carboxaldehyde [3.4 g; J. Chem. Soc. C 779 (1967)] in ethanol (60 ml) was added sodium borohydride (0.34 g). After 10 minutes the solution was poured onto water (200 ml) and extracted with ether (2×50 ml). The ether extracts were washed with water (2×25 ml), dried and then evaporated to the title product as an orange oil. Yield, 3.4 g. 'HNMR (CDCl3, 60 MHz): 2.6 (s, 1H), 3.8 (s, 3H), 4.8 (s, 2H), 7.0-8.0 (m, 4H). This material (1.5 g) was dissolved in ether (20 ml). To the solution cooled in an ice-bath was added phosphorous tribromide (0.7 ml). The mixture was let to stand for 1 hour. The reaction mixture was poured onto ice-water (50 ml) and the ether layer separated, collected, dried and evaporated to obtain the title product as a light yellow oil (yield, 1.4 g). 'HNMR CDCl3, 60 MHz): 4.0 (s, 3H), 5.0 (s, 2H), 7.2-7.8 (m, 4H).

1. additionAfter 10 minutes the solution was poured onto water (200 ml)
2. extractionextracted with ether (2×50 ml)
3. washThe ether extracts were washed with water (2×25 ml)
4. customdried
5. customevaporated to the title product as an orange oil
6. customYield
7. temperatureTo the solution cooled in an ice-bath
8. additionThe reaction mixture was poured onto ice-water (50 ml)
9. customthe ether layer separated
10. customcollected
11. customdried
12. customevaporated

ORD record

ord-5f09bf94869544988a0a6a89f64edacf

Source dataset

uspto-grants-1990_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04939140