6-Methylbenzo[b]thiophene-3-carboxylic acid synthesis

4synthesis methods

Product Name:6-Methylbenzo[b]thiophene-3-carboxylic acid
CAS Number:82787-84-6
Molecular formula:C10H8O2S
Molecular Weight:192.23

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6-Methylbenzo[b]thiophene-3-carboxylic acid

82787-84-6
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Yield:-

Reaction Conditions:

with n-butyllithium;carbon dioxide in hexane;water;

Steps:

7.iii (iii)

(iii) 6-Methylbenzo[b]thiophene-3-carboxylic acid A solution of n-butyl lithium (15 ml. of 1.0 M solution in hexane) was added dropwise to a stirred solution of 3-bromo-6-methylbenzo[b]thiophene (3.0 g.) in dry ether (40 ml.) at -70° C. under an atmosphere of dry nitrogen. The mixture was stirred at -70° C. for 30 minutes and then an excess of crushed solid carbon dioxide was added. When all the carbon dioxide had evaporated, water (25 ml.) was added and the mixture was stirred for a few minutes. The organic layer was separated and washed with 2 N.NaOH solution. The aqueous layer and NaOH extract were combined and acidified with concentrated hydrochloric acid. The solid was filtered off, washed with water, dried and crystallized from toluene to give 6-methylbenzo[b]thiophene-3-carboxylic acid (1.60 g.), m.p. 205°-209°. Analysis: Found: C, 62.31; H, 4.17. C₁₀ H₈ O₂ S Requires: C, 62.48; H, 4.20%.

References:

US4410539,1983,A

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References

Benzo[b]thiophene, 2,3-dibromo-6-methyl-

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References

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References