METHYL 4-BROMO-3-FLUOROBENZOATE 98 Chemical Properties

Melting point:

64-66

Boiling point:

270.1±25.0 °C(Predicted)

Density 

1.577±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Light yellow

InChI

InChI=1S/C8H6BrFO2/c1-12-8(11)5-2-3-6(9)7(10)4-5/h2-4H,1H3

InChIKey

WDAFDKXHLVMFKA-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=C(Br)C(F)=C1

Safety Information

Hazard Codes 

Xi

RIDADR 

2811

Hazard Note 

Irritant/Keep Cold

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2916310090

METHYL 4-BROMO-3-FLUOROBENZOATE 98 Usage And Synthesis

Uses

Methyl 4-bromo-3-fluorobenzoate is a carboxylic acid ester derivative and an intermediate in the preparation of various drugs.

Chemical Properties

off-white powder

Synthesis

Step 2: Under nitrogen protection, 1-methylpiperazine (980 μL, 8.80 mmol) was dissolved in toluene (15 mL), and tris (dibenzylideneacetone) dipalladium (201 mg, 0.22 mmol), BINAP (550 mg, 0.88 mmol), and cesium carbonate (4.30 g, 13.2 mmol) were added sequentially. The reaction mixture was stirred at room temperature for 30 min before adding methyl 4-bromo-3-fluorobenzoate (2.05 g, 8.80 mmol). Subsequently, the reaction system was heated to 105 °C with continuous stirring for 18 hours. After completion of the reaction, the mixture was cooled to room temperature, filtered through a diatomaceous earth pad and the filter cake was washed with ethyl acetate. The filtrates were combined and concentrated under reduced pressure to give an orange oily crude product. The crude product was purified by silica gel column chromatography using 5% dichloromethane solution of methanol as eluent. The target fraction was collected and concentrated under reduced pressure to afford methyl 3-fluoro-4-(4-methylpiperazin-1-yl)benzoate (1.80 g, 81%) as a colorless oil. The structure of the product was confirmed by 1H NMR (400 MHz, CD3OD) and mass spectrometry (EI): 1H NMR (400 MHz, CD3OD): δ 7.78-7.73 (d, 1H), 7.64-7.59 (d, 1H), 7.09-7.03 (m, 1H), 3.86 (s, 3H), 3.26-3.20 (m, 4H), 2.65-2.59 (m, 4H), 2.35 (s, 3H). MS (EI): m/z 253 (MH+).

References

[1] Patent: US2010/216806, 2010, A1. Location in patent: Page/Page column 103
[2] Patent: WO2009/55077, 2009, A1. Location in patent: Page/Page column 369
[3] Patent: US2009/23748, 2009, A1. Location in patent: Page/Page column 21
[4] Patent: US2012/230951, 2012, A1. Location in patent: Page/Page column 97-98
[5] Patent: WO2016/20836, 2016, A1. Location in patent: Page/Page column 101; 102

METHYL 4-BROMO-3-FLUOROBENZOATE 98(849758-12-9)Related Product Information

• METHYL 4-BROMO-3-METHOXYBENZOATE
• Methyl 4-bromo-3-methylbenzoate
• METHYL 4-BROMO-3-HYDROXYBENZOATE
• Methyl 4-BroMo-5-chloro-2-furoate
• Methyl dihydrojasmonate
• METHYL 4-BROMO-2-HYDROXYBENZOATE
• BENZOIC ACID, 4-AMINO-2-BROMO-, METHYL ESTER
• 4-BroMo-2-iodo-benzoic acid Methyl ester
• METHYL 4-BROMO-3-FLUOROBENZOATE 98
• 4-Bromo-3-fluorobenzoic acid
• 3-BROMO-4-FLUORO-BENZOIC ACID METHYL ESTER
• METHYL 2-BROMO-5-FLUOROBENZOATE
• METHYL 2-BROMO-4-FLUOROBENZOATE
• METHYL 3-BROMO-5-FLUOROBENZOATE
• 4-BROMO-3-FLUOROBENZOIC ACID ETHYL ESTER
• TERT-BUTYL 4-BROMO-3-FLUOROBENZOATE
• TERT-BUTYL 4-BROMO-2,3,5,6-TETRAFLUOROBENZOATE
• RARECHEM AL BI 1308