Water → HCID 13663047, compound

A solution of 6-bromo-3-chlorobenzo[b]thiophene-2-carboxylic acid chloride (6.20 g) in dry ether (50 ml) and dry tetrahydrofuran (50 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (0.58 g) in dry ether (250 ml) at 0° under an atmosphere of dry nitrogen. The mixture was stirred at room temperature for 30 minutes and then at reflux for 21/2 hours before being cooled and allowed to stand for 18 hours. It was then cooled and the excess of lithium aluminium hydride was decomposed by the cautious addition of water (1.0 ml) followed by 5N sodium hydroxide (1.0 ml) followed by water (2.0 ml) with vigorous stirring. The mixture was filtered and the filtrate was evaporated to give a solid which was chromatographed on silica gel. Elution with chloroform first gave some impurity followed by pure product. The product containing fractions were combined and evaporated to give a solid which was crystallised from chloroform to give 6-bromo-3-chloro-2-hydroxymethylbenzo[ b]thiophene (2.22 g), m.p. 117°-118°.

1. temperatureat reflux for 21/2 hours
2. temperaturebefore being cooled
3. waitto stand for 18 hours
4. temperatureIt was then cooled
5. filtrationThe mixture was filtered
6. customthe filtrate was evaporated
7. customto give a solid which
8. customwas chromatographed on silica gel
9. washElution with chloroform
10. customfirst gave some impurity
11. additionThe product containing fractions
12. customevaporated
13. customto give a solid which
14. customwas crystallised from chloroform

ORD record

ord-2215253d5e9d4aca8d62f81213b2a120

Source dataset

uspto-grants-1986_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04590200