ChemicalBook CAS DataBase List 2-BROMO-5-HYDROXYBENZALDEHYDE

2-BROMO-5-HYDROXYBENZALDEHYDE synthesis

10synthesis methods

Product Name:2-BROMO-5-HYDROXYBENZALDEHYDE
CAS Number:2973-80-0
Molecular formula:C7H5BrO2
Molecular Weight:201.02

100-83-4

2973-80-0

General procedure for the synthesis of 2-bromo-5-hydroxybenzaldehyde from m-hydroxybenzaldehyde: 3-hydroxybenzaldehyde (120 g, 0.98 mol) was suspended in 2400 mL of dichloromethane (CH2Cl2) in a 5 L four-necked, round-bottomed flask fitted with an overhead stirrer, a temperature probe, a dosing funnel, and a condenser tube. The mixture was heated to 35-40 °C to completely dissolve the raw material. Bromine (52 mL, 1.0 mol, 1.02 eq.) was added slowly dropwise through the addition funnel, controlling the rate of dropwise acceleration to maintain the reaction temperature between 35-38°C. After dropwise addition, the reaction mixture was stirred at 35 °C overnight. Subsequently, the mixture was slowly cooled to -5-0 °C over a period of 2 h and stirring was continued for 1 h at this temperature. The precipitated solid was collected by filtration through a Brinell funnel and the filter cake was washed with 400 mL of cold 1:1 n-heptane/dichloromethane mixture. The resulting gray solid was dried under vacuum at room temperature (0.2 mmHg). The yield was 124.3 g in 63% yield.

7507-86-0 Synthesis

7507-86-0
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2973-80-0
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Yield:2973-80-0 90.9%

Reaction Conditions:

with boron tribromide in dichloromethane at 0 - 25; for 3 h;

Steps:

343B.1

To a mixture of 2-bromo-5-methoxybenzaldehyde (2000.0 mg, 9.3 mmol) indichioromethane (10 mL) was added boron tribromide (2M in DCM; 4.65 mL, 9.3 mmol) slowly at 0 °C. The reaction was warmed up to 25 °C and stirred for 3 h. The reaction was quenched with water (10 mL) at 0°C and extracted with EtOAc (50 mL). The organic layer was washed with water (50 mL x 2) and brine (50 mL), dried over Mg504 and concentrated. The residue was purified by flash column chromatography (petroleum ether) to afford 2-bromo-5-hydroxybenzaldehyde (1.7 g, 90.9% yield) as a colorless oil.

References:

WO2017/84630,2017,A1 Location in patent:Paragraph 00976

100-83-4
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2973-80-0
408 suppliers
$6.00/1g

References

14472-14-1 Synthesis