3-BROMO-2-METHYL-BENZOIC ACID METHYL ESTER Chemical Properties

Melting point:

29 °C

Boiling point:

140°C/21mmHg(lit.)

Density 

1.433±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform

form 

Solid

color 

White

InChI

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

InChIKey

MKQQTCSBXHAYQL-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=CC(Br)=C1C

Safety Information

HS Code 

2916399090

3-BROMO-2-METHYL-BENZOIC ACID METHYL ESTER Usage And Synthesis

Uses

3-Bromo-2-methylbenzoic Acid Methyl Ester is a compound useful in organic synthesis.

Chemical Properties

White Solid

Synthesis

3-Bromo-2-methylbenzoic acid (16 g, 74.4 mmol) and iodomethane (21.2 g, 148.8 mmol) were reacted in DMF (160 mL) in the presence of sodium bicarbonate (12.5 g, 148.8 mmol). The reaction mixture was heated and stirred at 60 °C for 2 hours. After the reaction was completed, the mixture was cooled to room temperature and slowly poured into ice water (400 mL). The aqueous phase was extracted with ethyl acetate (4 x 100 mL) and the organic phases were combined. The organic phase was washed sequentially with water (3 x 100 mL) and saturated saline (100 mL) and then dried with anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give methyl 3-bromo-2-methylbenzoate (17.6 g, 100% yield) as an oil. The product was characterized by 1H NMR (CDCl3): δ 7.70 (t, J = 7.6 Hz, 2H), 7.08 (t, J = 7.9 Hz, 1H), 3.90 (s, 3H), 2.67 (s, 3H).

References

[1] Patent: US2003/96841, 2003, A1
[2] Patent: US2014/179667, 2014, A1. Location in patent: Paragraph 0802; 0803
[3] Patent: WO2008/65199, 2008, A1. Location in patent: Page/Page column 74

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