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ChemicalBook CAS DataBase List 5-Fluoro-2-nitrophenylacetic acid

5-Fluoro-2-nitrophenylacetic acid synthesis

4synthesis methods
synthesis of 5-Fluoro-2-nitrophenylacetic acid: To a mixture of 23.2g of 3-fluorophenylacetic acid and 100ml. of conc. sulfuric acid is added dropwise 6.5ml. of conc. nitric acid while maintaining the tempera ture below 40°C. The mixture is stirred at ambient temperature for 24 hours and then poured onto one kilogram of ice. The resulting precipitate is recovered by filtering, washed with water and dried in vacuo to obtain crude 5-fluoro-2-nitrophenylacetic acid, m.p. 137-142°C.
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Yield:29640-98-0 87%

Reaction Conditions:

with ammonium nitrate;trifluoroacetic anhydride in chloroform at 0; for 3 h;

Steps:

15 Preparation 15; (5-FLUORO-2-NITRO-PHENYL)-ACETIC ACID
3-methyl phenethyl alcohol (5 g, 36.7 MMOL) was diluted in 30 mL of chloroform and ammonium nitrate (3.12 g, 38.9 MMOL) was added. The reaction mixture was cooled to 0 °C and trifluor acetic acid anhydride (16.02 mL, 113 MMOL) was added dropwise. The reaction stirred at 0 °C for 3 hours before water was added to slowly quench the reaction. The chloroform layer was washed with water then collected and dried over NA2SO4 then concentrated. The desired isomer crystallized out of the crude solution in ethyl acetate and was then triturated with acetonitrile to afford 5.25 g of the desired isomer as a brown solid. Yield 87%; MS (APCI) : 199 [M-H]-.

References:

WARNER-LAMBERT COMPANY LLC WO2004/41793, 2004, A1 Location in patent:Page 58

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