Cyanic acid, 4-formylphenyl ester (9CI) synthesis
- Product Name:Cyanic acid, 4-formylphenyl ester (9CI)
- CAS Number:1126-84-7
- Molecular formula:C8H5NO2
- Molecular Weight:147.13
Yield:1126-84-7 88%
Reaction Conditions:
with triethylamine in tetrahydrofuran at 0 - 20; for 6 h;
Steps:
2.1 Synthesis of cyano reagents
Following the reported procedure, [4-5] to a solution of cyanogen bromide (1.2 equiv) in THF (20 mL) was added slowly a solution of phenol (1.0 equiv) with triethylamine (3.0 equiv) in THF (20 mL) at 0 °C. The reaction mixture was stirred for 2 h at 0 °C and then at rt for 4 h. Filtered on a celite pad and concentrated in vacuum, the residue was dissolved in ethyl acetate and petroleum ether (1:5) for re-crystallization to get the colorless solid. 4-Cyanatobenzaldehyde (2a): White solid, 88% yield, m.p. 109-111 °C. 1H NMR (400 MHz, CDCl3): δ = 10.02 (s, 1H), 8.02 (d, J = 8.0 Hz, 2H), 7.49 (d, J = 8.0 Hz, 2H) ppm; 13C NMR (100 MHz, CDCl3): δ = 189.7, 156.2, 134.9, 132.1, 116.0, 107.6 ppm.
References:
Karmaker, Pran Gopal;Qiu, Jiashen;Wu, Di;Zhang, Sule;Yin, Hongquan;Chen, Fu-Xue [Tetrahedron Letters,2018,vol. 59,# 21,p. 2034 - 2037] Location in patent:supporting information
