4-CHLORO-4'-(METHYLTHIO)BENZOPHENONE synthesis
- Product Name:4-CHLORO-4'-(METHYLTHIO)BENZOPHENONE
- CAS Number:72585-17-2
- Molecular formula:C14H11ClOS
- Molecular Weight:262.75
100-68-5
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122-01-0
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72585-17-2
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Yield:72585-17-2 87%
Reaction Conditions:
Stage #1: 4-chloro-benzoyl chloridewith aluminum (III) chloride in dichloromethane at 0; for 0.25 h;
Stage #2: methyl-phenyl-thioether in dichloromethane at 0 - 20; for 24 h;
Steps:
15 4.18 4′-Chloro-4-methylthiobenzophenone (24)
To a solution of 123 4-chlorobenzoyl chloride (1.02mL, 8.07mmol) in 20mL of 133 dichloromethane cooled at 0°C was added 148 aluminium chloride (1.28g, 9.63mmol) and the mixture was stirred for 15min. Next, the 24 thioanisole (0.95mL, 8.17mmol) was added and the resulting mixture was stirred at room temperature for 24h. The solution was washed with H2O (3×20mL) and the organic layers were dried with Na2SO4, filtered off and the filtrate was concentrated under reduced pressure. The product 35 24 was obtained as a white solid. 87% (1.84g) yield; mp: 120-123°C (hexane/ethyl acetate). IR (ATR diamond, cm-1) ν: 1636, 1585, 1283, 749; 1H NMR (400MHz, CDCl3) δ: 2.54 (s, 3H, SCH3), 7.25 (d, J=9Hz, 2H, H-2, H-6), 7.26 (d, J=8Hz, 2H, H-3′, H-5′), 7.46 (d, J=9Hz, 2H, H-3, H-5), 7.74 (d, J=8Hz, 2H, H-2′, H-6′); 13C NMR (100MHz, CDCl3) δ: 15.9 (CH3), 124.2 (2CH), 128.9 (2CH), 130.6 (2CH), 130.7 (2CH), 133.4 (Cq), 136.4 (Cq), 139.5 (Cq), 146.1 (Cq), 194.8 (Cq). HRMS (ESI): calcd for C14H12ClOS [M+H]+: 263.0297 found 263.0299.
References:
Navarro, Lorena;Rosell, Gloria;Sánchez, Silvia;Boixareu, Núria;Pors, Klaus;Pouplana, Ramon;Campanera, Josep M.;Pujol, M. Dolors [Bioorganic and Medicinal Chemistry,2018,vol. 26,# 14,p. 4113 - 4126]
104-88-1
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72585-17-2
19 suppliers
$294.00/1g
74-11-3
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72585-17-2
19 suppliers
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100-68-5
332 suppliers
$9.00/1g
122-01-0
363 suppliers
$13.00/25g
951888-05-4
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72585-17-2
19 suppliers
$294.00/1g