ChemicalBook CAS DataBase List 4-AMINO-2-FLUOROBENZONITRILE

4-AMINO-2-FLUOROBENZONITRILE synthesis

10synthesis methods

Product Name:4-AMINO-2-FLUOROBENZONITRILE
CAS Number:53312-80-4
Molecular formula:C7H5FN2
Molecular Weight:136.13

4-Amino-2-fluorobenzonitrile is an organic intermediate that can be prepared by the reaction of 4-bromo-3-fluoroaniline with Zn(CN)2.

557-21-1 Synthesis

557-21-1
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656-65-5 Synthesis

656-65-5
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53312-80-4
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Yield: 72%

Reaction Conditions:

with tetrakis(triphenylphosphine) palladium⁽⁰⁾ in N,N-dimethyl-formamide at 26 - 130; for 16 h;Inert atmosphere;

Steps:

Intermediate 100: 4-amino-2-fluorobenzonitrile:
To a solution of 4-bromo-3-fluoroaniline (5.0 g, 26.46 mmol, commercial source: Matrix) in N,N- dimethylformamide (50 mL), Zn(CN)₂(9.3 g, 79.38 mmol, commercial source: Sigma Aldric ) was added at 26 °C. The reaction mixture was purged with nitrogen for 10 min, tetrakis(triphenylphosphine)palladium(0) (6.1 g, 5.29 mmol, commercial source: Alfa Aesar) was added and purged again with nitrogen for 10 minutes at 26 °C. The resultant reaction mixture was stirred at 130 °C for 16 h. Upon completion, the reaction mixture was cooled to 26 °C and diluted with ethyl acetate (2x500 mL). The organic layer was washed with water (2x100 mL), dried over anhydrous Na₂S04, filtered and the filtrate was evaporated under reduced pressure. The crude was purified by column chromatography using silica (100-200 mesh), eluted with 15% ethyl acetate in petroleum ether. The pure fractions were concentrated under reduced pressure to afford 4- amino-2-fluorobenzonitrile (2.7 g, 72%) as an off white solid.¹H NMR (400 MHz, CDCI₃) δ 7.38- 7.31 (m, 1 H), 6.47-6.38 (m, 2H), 4.26 (br s, 2H). MS m/z [M+H]⁺= 137.06

References:

GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED;ALEMPARTE-GALLARDO, Carlos;ENCINAS, Lourdes;ESQUIVIAS PROVENCIO, Jorge WO2019/34729, 2019, A1 Location in patent:Page/Page column 83

34667-88-4 Synthesis