(6-fluorobenzo[b]thiophen-2-yl)methanol synthesis

2synthesis methods

Product Name:(6-fluorobenzo[b]thiophen-2-yl)methanol
CAS Number:212078-70-1
Molecular formula:C9H7FOS
Molecular Weight:182.21

Benzo[b]thiophene-2-carboxylic acid, 6-fluoro-, ethyl ester

212078-68-7
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212078-70-1
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Yield:212078-70-1 74%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 20; for 3 h;

Steps:

Synthesis of 6-fluoro-benzo[b]thiophen-2-yl)-methanol

To a suspension of lithium aluminum hydride (15.5 g, 0.43 mol) in dry THF (600 ml) was added a solution of 6-fluoro-benzo[b]thiophene-2-carboxylic acid ethyl ester (96.49 g, 0.43 mol) in dry THF (960 ml), the mixture was stirred for 3 h at 20° C. The reaction was carefully quenched by the dropwise addition of water (15.5 ml), 15% NaOH (15.5 ml) and water (46.5 ml), stirred for 0.5 h, then filtered and washed with THF:water (1:1) (100 ml). The filtrate was concentrated to give 58.25 g (74%) of 6-fluoro-benzo[b]thiophen-2-yl)-methanol as white powder. ¹H-NMR (400 MHz, DMSO-d6); δ (ppm): 4.67 (s, 2H), 5.51 (s, 1H), 7.17 (t, 1H), 7.22 (s, 1H), 7.72-7.80 (m, 2H).

References:

US2014/303207,2014,A1 Location in patent:Paragraph 0284

1550-35-2 Synthesis

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References