ChemicalBook CAS DataBase List 6-Fluorochromane-2-carboxylic acid

6-Fluorochromane-2-carboxylic acid synthesis

6synthesis methods

Product Name:6-Fluorochromane-2-carboxylic acid
CAS Number:99199-60-7
Molecular formula:C10H9FO3
Molecular Weight:196.18

99199-59-4
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$34.46/1g

99199-60-7
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Yield:99199-60-7 90%

Reaction Conditions:

with palladium on activated charcoal;hydrogen;acetic acid at 75 - 80;Inert atmosphere;Autoclave;

Steps:

Preparation of 6-Fluoro-3, 4-dihydro-2H-1-benzopyran- 2-carboxylic acid (6):

Charged compound 5 (10.0 g) in 500 mL autoclave reactor and Pd/C (0.5 g) in acetic acid (150 ml) under nitrogen atmosphre, applied 15-20 kg Hydrogen pressure, and heated at 75-80 °C for 30-35 hrs. Complition of reaction was monitered over TLC. Cool, filter and washed with acetic acid 25 ml. Concentrate the reaction mass under reduced pressure. Charge toluene in deggased mass and aq. NaOH Solution (2.28g in 30 ml water), stir for 30 min and separated aq. and toluene layer. Aq. layer acidified with conc. HCl to get solid compound. Filter, washed with water and dry to get compound 8.47 g (6). 6-Fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid (6) Yield: 90.00 %, Colour: Light yellow Solid, Molecular Formula: C₁₀H₉FO₃, Mol. Wt.: 196.17g mol^-1, Elemental composition (%): Calculated: C, 61.22; H, 4.62; F, 9.68; O, 24.47, Found: C, 61.28; H, 4.58; F, 9.66; O, 24.48, ¹H NMR (400 MHz, CDCl₃, ppm): δ = 8.61(Bs, 1H, HO-Acid), 6.76-7.01(m, 3H, H-Ar), 4.78(t, 1H, Methine), 2.85-2.82(t, -CH₂-CH₂-Ar, J=12 Hz), 2.37-2.14(m, 2H, -CH₂-CH₂-Ar), ¹³C NMR (400 MHz, CDCl₃, ppm): δ = 175.2, 158.4, 156.0, 149.0, 122.4-122.3, 117.9-117.8, 115.5-115.2 73.2, 24.1-23.5, MS (ESI): m/z 196.18 (M).

References:

Dongare, Balasaheb B.;Ghanwat, Anil A.;Kashid, Bharat B.;Khedkar, Vijay M.;More, Kishor R.;Salunkhe, Pravin H. [Bioorganic and medicinal chemistry letters,2020] Location in patent:supporting information

874649-82-8 Synthesis