METHYL 2-BROMO-5-METHYLBENZOATE Chemical Properties

Boiling point:

270.1±20.0 °C(Predicted)

Density 

1.433±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C9H9BrO2/c1-6-3-4-8(10)7(5-6)9(11)12-2/h3-5H,1-2H3

InChIKey

PYRAZCQFEMNXJA-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC(C)=CC=C1Br

Safety Information

HS Code 

2916399090

METHYL 2-BROMO-5-METHYLBENZOATE Usage And Synthesis

Synthesis

Step 1: Preparation of methyl 2-bromo-5-methylbenzoate Oxalyl chloride (0.13 mL, 1.5 mmol) was slowly added to a mixed solution of dichloromethane (DCM, 4 mL) and N,N-dimethylformamide (DMF, 1 drop) of 2-bromo-5-methylbenzoic acid (215 mg, 1.0 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 1 hour before oxalyl chloride (0.13 mL, 1.5 mmol) was added again. After continued stirring for 1 hour, methanol (MeOH, 2 mL) was added and the reaction mixture continued to stir for 6 hours. Upon completion of the reaction, the pH was adjusted to 9 with sodium carbonate (Na2CO3) solution and extracted with dichloromethane (DCM, 2 x 10 mL). The organic layers were combined, washed with saturated saline, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford methyl 2-bromo-5-methylbenzoate (210 mg, 92% yield) as a colorless oil using petroleum ether-ethyl acetate (PE-EA, 15:1) as eluent. 1H NMR (400 MHz, CDCl3): δ 7.60 (d, J = 1.6 Hz, 1H), 7.53 (d, J = 8.8 Hz, 1H), 7.15 (q, J = 3.2 Hz, 1H), 3.92 (s, 3H), 2.33 (s, 3H) ppm.

References

[1] Tetrahedron, 2014, vol. 70, # 14, p. 2383 - 2388
[2] Patent: CN105461699, 2016, A. Location in patent: Paragraph 0739; 0740; 0741; 0742; 0743
[3] Patent: WO2013/9259, 2013, A1. Location in patent: Page/Page column 90; 91
[4] Patent: WO2013/36196, 2013, A1. Location in patent: Page/Page column 95
[5] Patent: US2013/131016, 2013, A1. Location in patent: Paragraph 0199

METHYL 2-BROMO-5-METHYLBENZOATE(90971-88-3)Related Product Information

• Ethyl 4-Hydroxy-2-Methylbenzoate
• Methyl4-amino-2-methylbenzoate
• 3-BROMO-2-METHYL-BENZOIC ACID METHYL ESTER
• METHYL 4-CHLORO-3-METHYLBENZOATE
• ETHYL 3-METHYL-4-NITROBENZOATE
• 5-AMINO-2-METHYL-BENZOIC ACID METHYL ESTER
• Methyl 5-Methyl-2-Nitrobenzoate
• Ethyl 3-bromo-4-methylbenzoate
• Methyl-5-amino-2-chlorobenzoate
• AKOS BB-3093
• METHYL 2-AMINO-5-METHYLBENZOATE
• BENZOIC ACID,4-BROMO-2-METHYL-,METHYL ESTER
• 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid Ethyl Ester
• Methyl 4-hydroxy-2-methylbenzoate
• ETHYL 2-AMINO-5-METHYLBENZOATE
• Methyl 2-Methyl-4-nitrobenzoate
• 4-AMINO-2-METHYLBENZOIC ACID ETHYL ESTER
• Ethyl 4-Bromo-3-methylbenzoate