Electric Literature of 575-03-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 575-03-1, name is 7-Hydroxy-4-(trifluoromethyl)coumarin, molecular formula is C10H5F3O3, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
[Syntheses of 6a and 6b] ; The compounds 6 and 6b were synthesized in the same manner. Firstly, triethylamine (1.1 eq) was added to a suspension of 7-hydroxy-4-(trifluoromethyl)coumarin (1.0 g) and 2,4-dinitrobenzenesulfon 1 chloride or, 2-nitro-4-(trifluoromethyl)benzenesulfonyl chloride (1.1 eq) in dichloromethane (20 mL) at 0°C. Next, the obtained mixed solution was stirred at room temperature for 1 hour. The reaction solution was diluted with dichloromethane (200 mL), was washed with 1M hydrochloric acid (200 mL) and saturated saline (200 mL), and was dried over magnesium sulfate. The residue obtained by evaporating the solvent under a reduced pressure was refined by silica gel column-chromatography (dichloromethane), thereby obtaining each objective compound. Yields and instrumental analytical values of these compounds will be described below. 6a: 1.9 g (95percent) as a white crystal. m.p. 123-124.5° C (from benzene). 1H-NMR(270 MHz, [D]6-DMSO, TMS): delta= 9.13 (d, 4JH,H=2.3 Hz, 1H; aromatic), 8.64 (dd, 3JH,H= 8.7 Hz, 4JH,H=2.3 Hz, 1H; aromatic), 8.35 (d, 3JH,H= 8.7 Hz, 1H; aromatic), 7.79 (dd, 3JH,H=8.9 Hz, 8JH,H=1.5 Hz, 1H; aromatic), 7.54 (d, 4JH,H=2.5 Hz, 1H, aromatic), 7.32 (dd, 3JH,H=8.9, 4JH,H= 2.5 Hz, 1H; aromatic), 7.15 (s, 1H; aromatic). FTIR (KBr): nu = 1751 (CO, s), 1558(NO2, s), 1542 (NO2, s)cm-1. Elemental analysis (percent) calcd for C16H7 F3N2O9S: C 41.75, H 1.53, N6.09; found: C 41.74, H 1.63, N 5,92. FAB HRMS calcd for C16H8F3N2O9S (MH+): 460.9903; found: 460.9888. 6b: 2.0 g (95percent) as a white crystal. m.p. 134.5-136°C (from AcOEt-hexane). 1H-NMR (270 MHz, [D]6-DMSO, TMS): delta = 5.82 (s, 1H; aromatic), 8.33 (d, 4JH,H = 1.5 Hz, 2H; aromatic), 7.83 (dd, 3JH,H= 8.9 Hz, 4JH,H= 1.8 Hz, 1H; aromatic), 7.57 (t, 4JH,H= 2.2 Hz, 1H; aromatic), 7.34 (dt, 3JH,H= 8.9 Hz, 4JH,H= 2.2 Hz, 1H, aromatic), 7.15 (s, 1H; aromatic). FTIR (KBr): nu = 1752 (CO, s), 1557 (NO2, s) cm-1. Elemental analysis (percent) calcd for C17H7F6NO7S: C 42.25, H 1.46, N 2.90; found: C 42.24, H 1.55, N 2.72. FAB HRMS calcd for C17H8F6NO7S (MH+): 483.9926; found: 483.9925.
While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 575-03-1, 7-Hydroxy-4-(trifluoromethyl)coumarin.
Reference:
Patent; Osaka Industrial Promotion Organization; EP1650200; (2006); A1;,
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