5-Fluoro-furan-2-carboxylic acid synthesis
- Product Name:5-Fluoro-furan-2-carboxylic acid
- CAS Number:377729-87-8
- Molecular formula:C5H3FO3
- Molecular Weight:130.07
1333218-13-5
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Yield:377729-87-8 95%
Reaction Conditions:
with 10% Pd/C;hydrogen in methanol at 20; under 760.051 Torr; for 0.5 h;
Steps:
Preparation of 1: To a solution of 11c (0.220 g, 1.00 mmol) in MeOH (10 mL) was added 10% Pd/C (50% wet, 22 mg). The resulting suspension was stirred at rt under hydrogen atmosphere (balloon, 1 atm) for 30 min (reaction was monitored by TLC; prolonged reaction time resulted in de-fluoronation). The reaction mixture was filtered through a short pad of diatomaceous earth and the filter cake was washed with methanol (10 mL). The filtrate was concentrated under reduced pressure. The residue was triturated with a mixture of hexanes (4 mL) and methylene chloride (2 mL), filtered, and dried under high vacuum to give 1 (0.123 g, 95%) as a white solid: 1H NMR (300 MHz, CD3OD) δ 7.20 (t, J = 3.5 Hz, 1H), 5.81 (dd, J = 7.0, 3.5 Hz, 1H); 13C NMR (75 MHz, CD3OD) δ 160.7, 160.2 (d, J = 281 Hz), 137.1, 121.6, 86.0 (d, J = 13.6 Hz); 19F NMR (282 MHz, CD3OD) δ 110.8.
References:
Song, Renhua;Lin, Weimin;Jiang, Qin [Tetrahedron Letters,2011,vol. 52,# 38,p. 4965 - 4966] Location in patent:experimental part
22427-65-2
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645-12-5
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