3-broMo-6-hydroxy-2-Methylbenzaldehyde synthesis
- Product Name:3-broMo-6-hydroxy-2-Methylbenzaldehyde
- CAS Number:137644-94-1
- Molecular formula:C8H7BrO2
- Molecular Weight:215.04
137644-93-0
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Yield:137644-94-1 97.6%
Reaction Conditions:
with BBr3 in dichloromethane at 0; for 1.5 h;Inert atmosphere;
Steps:
17.2 17.2 Preparation of 3-bromo-6-hydroxy-2-methylbenzaldehyde
A solution of boron tribromide (13.1 g, 52.4 mmol, 5.1 mL, 1 eq) in dichloromethane (5 ml) was added to a stirred solution of 3-bromo-6-methoxy-2-methyl-benzaldehyde (12 g, 52.4 mmol, 1 eq) in DCM (150 mL) under nitrogen at 0°C. The reaction mixture was stirred for 1.5 hours at 0°C.TLC showed the reaction was completed. Water (400 mL) was added cautiously at 0°C and the mixture was continue stirred for 15 min. TLC showed the reaction was completed. The organic layer was washed with sodium bicarbonate aqueous (200 mL), water (200 mL) and brine (200 mL), then the organic layer was dried over sodium sulfate and concentrated under reduced pressure to give the crude product as brown solid which was purified by silica gel column chromatography (Petroleum ether/Ethyl acetate=100:1 to 50:1) to afford 3-bromo-6-hydroxy-2- methyl-benzaldehyde (11 g, 97.6% yield) as yellow solid.1H NMR (400 MHz, CDCl3) δ 12.07 (s, 1H), 10.37 (s, 1H), 7.64 (d, J = 8.8 Hz, 1H), 6.75 (d, J = 8.8 Hz, 1H), 2.69 (s, 3H).
References:
WO2022/133420,2022,A1 Location in patent:Paragraph 0251; 0253
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