5-Bromo-2-hydroxy-3-(trifluoromethyl)benzaldehyde synthesis
- Product Name:5-Bromo-2-hydroxy-3-(trifluoromethyl)benzaldehyde
- CAS Number:251300-30-8
- Molecular formula:C8H4BrF3O2
- Molecular Weight:269.02
336628-67-2
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251300-30-8
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Yield:251300-30-8 66%
Reaction Conditions:
with N-Bromosuccinimide in acetonitrile at 0; for 1 h;
Steps:
28.2 28.2 Preparation of 5-bromo-2-hydroxy-3-(trifluoromethyl)benzaldehyde
To a solution of 2-hydroxy-3-(trifluoromethyl)benzaldehyde (10.7 g, 56.3 mmol, 1 eq) in CH3CN (150 mL) was added NBS (12.0 g, 67.5 mmol, 1.2 eq) at 0oC. The mixture was stirred at 0°C for 1 h. TLC showed the reaction was completed. The reaction mixture was quenched by addition H2O (100 mL) at 0°C, and extracted with EtOAc (50 mL x 3). The combined organic layers were washed with brine (50 mL x 3), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate = 1/0 to 10/1) to give 5-bromo-2-hydroxy-3- (trifluoromethyl)benzaldehyde (10 g, 66.0% yield) as brown oil.1H NMR (CDCl3, 400 MHz) δ 11.63 (s, 1 H), 9.91 (s, 1 H), 7.93 (d, J = 2.4 Hz, 1 H), 7.89 (d, J = 2.4 Hz, 1 H).
References:
WO2022/133420,2022,A1 Location in patent:Paragraph 0288; 0290
50824-04-9
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100-97-0
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251300-30-8
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444-30-4
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251300-30-8
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336628-65-0
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251300-30-8
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336628-66-1
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251300-30-8
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