6-fluoro-2H-chromen-2-one synthesis
- Product Name:6-fluoro-2H-chromen-2-one
- CAS Number:75487-82-0
- Molecular formula:C9H5FO2
- Molecular Weight:164.13
Yield:75487-82-0 32%
Reaction Conditions:
with sulfuric acid at 150; for 1.5 h;
Steps:
Synthetic steps [26]
0.01mol of 4-fluorophenol, 0.01mol of maleic anhydride and 1mL of concentrated H2SO4 were mixed together. And the mixture was heated to 150°C for 1.5h. After cooling to room temperature, the reaction solution was diluted with 50mL of water and extracted four times with 20mL of ethyl acetate. The extracted liquid was dried with anhydrous magnesium sulfate, and then filtered and concentrated. The obtained crude product was further eluted and recrystallized from ethyl acetate for several times. Thus, we got 0.52g 6-fluoro coumarin and the yield was 32%. 1H NMR (DMSO, 600MHz) δ: 6.58 (d, J=9.6Hz,1H), 7.46(m,1H), 7.50(m,1H), 7.62(m, 1H); 8.04 (d, J=9.6Hz, 1H); 13C NMR (DMSO, 600MHz) δ: 114.12, 114.29, 117.88, 118.69, 118.75, 119.56, 119.72, 120.13, 120.20, 143.83, 143.85, 150.34, 150.36,157.69, 159.28, 160.21; IR (KBr) υ: 584, 887, 916, 1055, 1274, 1261, 1441, 1485, 1568, 1591, 1724, 3074cm-1.
References:
Bai, Yihui;Du, Jinyan;Weng, Xuexiang [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2014,vol. 126,p. 14 - 20]
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