(5-FLUORO-1-BENZOFURAN-2-YL)METHANOL synthesis

4synthesis methods

Product Name:(5-FLUORO-1-BENZOFURAN-2-YL)METHANOL
CAS Number:276235-91-7
Molecular formula:C9H7FO2
Molecular Weight:166.15

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276235-91-7
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Yield:276235-91-7 91%

Reaction Conditions:

with sodium tetrahydroborate;ethanol at 0 - 20;

Steps:

(5-fluorobenzofuran-2-yl)methanol (14); Compound 13 (180 mg, 1.10 mmol) was dissolved in EtOH (12 mL). NaBH₄ (45 mg, 1.21 mmol) was added portionwise at 0 °C, with vigorous stirring. The suspension was stirred at 0 °C for 15 min and then at room temperature for 1.5 h. Solvents were evaporated off in-vacuo. The crude residue was taken up in EtOAc and washed with water, brine and dried (MgSO₄). The solvent was evaporated off in vacuo. The residue was adsorbed on silica gel and purified by flash chromatography, eluting with hexane/EtOAc (3:1 ) to give 14 (150 mg, 91%) as a white solid. ¹H NMR (500MHz, CDCI₃): δ: 7.36 (1 H, d, J = 8.35 Hz, H-7), 7.19 (1 H, d, J = 7.80, H-4), 7.00 (1 H, t, J = 8.75 H-6), 6.60 (1 H, s, H-3), 4.75 (2H, s, CH₂).

References:

WO2010/125350,2010,A1 Location in patent:Page/Page column 40-41

93849-31-1 Synthesis