ChemicalBook CAS DataBase List 4-Cyano-3-fluorobenzoic acid

4-Cyano-3-fluorobenzoic acid synthesis

5synthesis methods

Product Name:4-Cyano-3-fluorobenzoic acid
CAS Number:176508-81-9
Molecular formula:C8H4FNO2
Molecular Weight:165.12

557-21-1 Synthesis

557-21-1
104 suppliers
$12.00/5g

153556-42-4
260 suppliers
$10.00/1g

176508-81-9
173 suppliers
$8.00/250mg

Yield:-

Reaction Conditions:

tetrakis(triphenylphosphine) palladium⁽⁰⁾ in N,N-dimethyl-formamide at 90; for 3 h;

Steps:

1.A
4-Cyano-3-fluorobenzoic acid: 4-Bromo-3-fluorobenzoic acid(7.5 g, 0.034 mol), Zn(CN)₂ (4.0 g, 0.034 mol) and Pd(PPh₃)₄ (3.95 g, 0.0034 mol) were added together with 60 mL of DMF (degassed). The mixture was heated at 90 ⁰C under N₂ for 3 h. It was cooled to room temperature and filtered to remove insoluble inorganic salts (discarded). The filtrate was diluted with water and extracted with EtOAc. The EtOAc mixture was washed with water, brine, dried over MgSO₄, and concentrated to yield 4.5 g of the desired product with 90% purity. This material was taken into the next step without further purification. ¹H-NMR (500 MHz, d₄-Me0H) δ 7.82 (m, IH), 7.90 (m, 3H), 7.56 (d, J= 10.0 Hz, IH), 7.68 (s, IH), 7.96 (d, J= 8.4 Hz, IH)

References:

BRISTOL-MYERS SQUIBB COMPANY WO2007/70826, 2007, A1 Location in patent:Page/Page column 121

268734-34-5 Synthesis