ChemicalBook CAS DataBase List methyl 3-bromo-5-fluoro-2-methylbenzoate

methyl 3-bromo-5-fluoro-2-methylbenzoate synthesis

6synthesis methods

Product Name:methyl 3-bromo-5-fluoro-2-methylbenzoate
CAS Number:1187318-53-1
Molecular formula:C9H8BrFO2
Molecular Weight:247.06

67-56-1

1187318-52-0

methyl 3-bromo-5-fluoro-2-methylbenzoate

1187318-53-1

At room temperature, 2-methyl-3-bromo-5-fluorobenzoic acid (4.2 g, crude) was dissolved in methanol (16 mL) and thionyl chloride (2.5 mL) was added slowly. The reaction mixture was heated to 70 °C with continuous stirring for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure by rotary evaporator to give the crude product. The crude product was purified by silica gel column chromatography with the eluent of petroleum ether/ethyl acetate (50:1, v/v) to afford methyl 3-bromo-5-fluoro-2-methylbenzoate (2.3 g, 51% yield) as a yellow oil.

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1187318-53-1
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Yield: 22 g

Reaction Conditions:

with N-Bromosuccinimide;sulfuric acid at 0 - 20; for 19 h;

Steps:

3.2 Step 2: Synthesis of Compound I-16C
Compound I-16B (15 g, 90 mmol) was added to a solution of concentrated sulfuric acid (200 mL).The ice bath was cooled to below 5 degrees Celsius and then NBS (17.8 g, 100 mmol) was added portionwise. The resulting mixture was stirred at 0 ° C for 3 hours, then at room temperature and stirred for 16 hours.Then slowly pour the mixture into ice water (2L).It was extracted with EtOAc (500 mL x 3).The combined organic layers were washed with water and brine.Drying and concentration gave Compound I-16C (22 g).

References:

Guangzhou Dankang Pharmaceutical Biological Co., Ltd.;Xu Yong;Huang Lu;Lin Dang;Hu Hai CN110092745, 2019, A Location in patent:Paragraph 0126-0128; 0132; 0133

1187318-52-0
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