4-((2-Chloro-4-fluorobenzyl)oxy)-benzene-1-sulfonyl chloride synthesis
- Product Name:4-((2-Chloro-4-fluorobenzyl)oxy)-benzene-1-sulfonyl chloride
- CAS Number:1036509-25-7
- Molecular formula:C13H9Cl2FO3S
- Molecular Weight:335.18
1430072-45-9
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Yield:1036509-25-7 88.6%
Reaction Conditions:
with oxalyl dichloride in dichloromethane;N,N-dimethyl-formamide at 0 - 20; for 48.2 h;Inert atmosphere;
Steps:
12 Sodium 4-(2-chloro-4-fluorobenzyloxy)benzenesulfonate (27)
4.1.12
4-(2-Chloro-4-fluorobenzyloxy)benzene-1-sulfonyl chloride (28)
To a 0 °C solution of oxalyl chloride (1.3 mL, 15.3 mmol) in dry CH2Cl2 (5.1 mL) under Ar atmosphere, N,N-dimetilformammide was added dropwise (1.2 mL, 15.3 mmol) followed by the sodium salt 27 (1.92 g, 5.11 mmol).
The reaction was stirred at 0 °C for 10 min and then at rt for 2 days.
The crude was poured into ice and the product was extracted with EtOAc.
Organic layers were washed with water, dried over Na2SO4 and concentrated in vacuo to give sulfonyl chloride 28 as a white solid (1.68 g, 88.6% yield).
1H NMR (CDCl3) δ: 5.22 (s, 2H), 7.00-7.23 (m, 4H); 7.49 (dd, J = 6.0 Hz, 1H); 7.98-8.02 (m, 2H).
References:
Nuti, Elisa;Santamaria, Salvatore;Casalini, Francesca;Yamamoto, Kazuhiro;Marinelli, Luciana;La Pietra, Valeria;Novellino, Ettore;Orlandini, Elisabetta;Nencetti, Susanna;Marini, Anna Maria;Salerno, Silvia;Taliani, Sabrina;Da Settimo, Federico;Nagase, Hideaki;Rossello, Armando [European Journal of Medicinal Chemistry,2013,vol. 62,p. 379 - 394]
45767-66-6
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