ChemicalBook CAS DataBase List 3-Bromo-2-fluorobenzoic acid methyl ester

3-Bromo-2-fluorobenzoic acid methyl ester synthesis

4synthesis methods

Product Name:3-Bromo-2-fluorobenzoic acid methyl ester
CAS Number:206551-41-9
Molecular formula:C8H6BrFO2
Molecular Weight:233.03

1007-16-5

74-88-4

3-Bromo-2-fluorobenzoic acid methyl ester

206551-41-9

To a 100 mL round-bottom flask was added 3-bromo-4-fluorobenzoic acid (5.00 g, 22.8 mmol, Oakwood), potassium carbonate (3.17 g, 22.9 mmol), and N,N-dimethylformamide (DMF, 30 mL). Subsequently, iodomethane (2 M in methyl tert-butyl ether (MTBE), 11.6 mL, 23.2 mmol) was slowly added and the reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the mixture was filtered and the filtrate was concentrated under reduced pressure. The obtained brown crude product was dissolved with ethyl acetate (EtOAc), filtered and concentrated again to finally obtain methyl 3-bromo-2-fluorobenzoate (4.76 g, 20.4 mmol, 89.5% yield) as a brown slurry, which could be used in subsequent steps without further purification.

1007-16-5
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$8.00/10g

74-88-4
356 suppliers
$15.00/10g

206551-41-9
148 suppliers
$9.00/250mg

Yield: 89.5%

Reaction Conditions:

with potassium carbonate in tert-butyl methyl ether;N,N-dimethyl-formamide at 20; for 16 h;

Steps:

2.1
To a 100 mL round bottom flask was added 3-bromo-2-fluorobenzoic acid (5.00 g, 22.8 mmol, Oakwood), potassium carbonate (3.17 g, 22.9 mmol), and DMF (30 mL).Iodomethane, 2 M in MTBE (11.6 ml, 23.2 mmol) was added and the reaction mixture was stirred at RT for 16 hours. The reaction was filtered and the filtrate concentrated was in vacuo. The resulting brown crude residue was taken up with EtOAc and again filtered and concentrated to give methyl 3-bromo-2-fluorobenzoate (4.76 g, 20.4 mmol, 89.5% yield), as a brown syrup that was used in the Step 2 without further purification.

References:

AMGEN INC. WO2007/61930, 2007, A1 Location in patent:Page/Page column 63

67-56-1 Synthesis