2-HYDROXY-5-(TRIFLUOROMETHOXY)BENZALDEHYDE synthesis
- Product Name:2-HYDROXY-5-(TRIFLUOROMETHOXY)BENZALDEHYDE
- CAS Number:93249-62-8
- Molecular formula:C8H5F3O3
- Molecular Weight:206.12
145742-65-0
93249-62-8
Step A: Boron tribromide (BBr3, 85.2 g, 341 mmol) was slowly added dropwise to a solution of 2-methoxy-5-(trifluoromethoxy)benzaldehyde (50.0 g, 227 mmol) in dichloromethane (DCM, 500 mL) at -20°C and under nitrogen protection. The reaction mixture was stirred at 0°C for 2 hours. Upon completion of the reaction, the reaction was quenched by the addition of ice chips, followed by pouring the mixture into an aqueous solution of saturated sodium bicarbonate (NaHCO3, 300 mL) and extracting with dichloromethane (DCM, 3 x 400 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated to give the crude product. The crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=20:1) to afford 2-hydroxy-5-(trifluoromethoxy)benzaldehyde (38.0 g, 81.0% yield). NMR hydrogen spectrum (400 MHz, CDCl3) δ 10.97 (s, 1H), 9.87 (s, 1H), 7.43-7.38 (m, 2H), 7.02 (d, J=8.0 Hz, 1H).
145742-65-0
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93249-62-8
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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
828-27-3
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93249-62-8
152 suppliers
$16.00/1g
710-18-9
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$5.00/1g
93249-62-8
152 suppliers
$16.00/1g