4-((4-chlorophenyl)thio)benzaldehyde synthesis
- Product Name:4-((4-chlorophenyl)thio)benzaldehyde
- CAS Number:137736-07-3
- Molecular formula:C13H9ClOS
- Molecular Weight:248.73
Yield:137736-07-3 76%
Reaction Conditions:
with potassium carbonate in N,N-dimethyl-formamide at 90; for 10 h;
Steps:
A mixture of 4-fluorobenzaldehyde (12.6 mmol, 1.57 g), 4-chlorobenzenethiol (12.6 mmol, 1.81 g), K2CO3 (15.1 mmol, 2.09 g) in DMF (5.00 mL) was heated at 90° C. for 10 h. After cooling to room temperature, the reaction mixture was poured into a separatory funnel with water (100 mL). The phases were separated and the aqueous layer was extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with water (2×100 mL), brine (50 mL) and dried over MgSO4. Removal of the solvents in vacuo gave a light yellow liquid. Purification by flash column chromatography (eluent: 5% EtOAc in Hexane) provided 4-(4-chlorophenylthio)benzaldehyde (2.00 g, 76.0% yield) as a light yellow liquid. 1H NMR (CDCl3) δ 9.93 (s, 1H), 7.72 (d, J=8.3 Hz, 2H), 7.46-7.39 (m, 4H), 7.25 (d, J=8.3 Hz, 2H).
References:
US2006/79523,2006,A1 Location in patent:Page/Page column 12
