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ChemicalBook CAS DataBase List 2-HYDROXY-5-(TRIFLUOROMETHOXY)BENZALDEHYDE
93249-62-8

2-HYDROXY-5-(TRIFLUOROMETHOXY)BENZALDEHYDE synthesis

3synthesis methods
-

Yield:93249-62-8 81%

Reaction Conditions:

with boron tribromide in dichloromethane at -20 - 0; for 2 h;Inert atmosphere;

Steps:

39.A

[00244] Step A: BBr3 (85.2 g, 341 mmol) was added dropwise at -20°C under N2 to a solution of 2-methoxy-5-(trifluoromethoxy)benzaldehyde (50.0 g, 227 mmol) in DCM (500 mL). The reaction mixture was stirred at 0°C for 2 hours. The reaction mixture was worked up by adding ice chips, then the mixture was poured into saturated aqueous NaHC03 (300 mL), and extracted with DCM (3 X 400 mL). The combined organic layers were dried and concentrated to afford the crude product, which was purified by silica gel (hexanes: EtOAc = 20:1) to give 2- hydroxy-5-(trifluoromethoxy)benzaldehyde (38.0 g, 81.0% yield). NMR (400MHz, CDC13) δ 10.97 (s, 1H), 9.87 (s, 1H), 7.43-7.38 (m, 2H), 7.02 (d, J = 8.0 Hz, 1 H).

References:

WO2013/148851,2013,A1 Location in patent:Paragraph 00244

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