METHYL 4-BROMO-3-METHOXYBENZOATE Chemical Properties

Melting point:

58-61

Boiling point:

172-173 °C

Density 

1.462±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder

color 

Lemony cream

InChI

InChI=1S/C9H9BrO3/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5H,1-2H3

InChIKey

XLKDKHRGIJWOSN-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant/Keep Cold

HS Code 

2918999090

METHYL 4-BROMO-3-METHOXYBENZOATE Usage And Synthesis

Synthesis Reference(s)

Tetrahedron Letters, 10, p. 1623, 1969 DOI: 10.1017/S0009838800024678

Synthesis

Step B. Synthesis of methyl 4-bromo-3-methoxybenzoate Methyl 4-bromo-3-hydroxybenzoate (27 mmol), potassium carbonate (33 mmol) and dimethyl sulfate (32 mmol) obtained from Step A were dissolved in acetone (40 mL) under nitrogen protection. The reaction mixture was heated to reflux temperature and stirred for 3 hours. After completion of the reaction, the mixture was cooled and the reaction was quenched by slowly adding 5 mL of water. Subsequently, the acetone was removed by rotary evaporator and diluted by adding 30 mL of water. The product in the aqueous phase was extracted with dichloromethane (3 × 20 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford the title compound methyl 4-bromo-3-methoxybenzoate (6.5 g, 99% yield) as a white crystalline solid.

References

[1] Patent: US2006/199806, 2006, A1. Location in patent: Page/Page column 23
[2] Patent: US2006/287522, 2006, A1. Location in patent: Page/Page column 24
[3] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2267 - 2273
[4] Yakugaku Zasshi, 1930, vol. 50, p. 224,227; dtsch. Ref. S. 26
[5] Chem.Abstr., 1930, p. 3513

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