METHYL 2-BROMO-5-METHOXYBENZOATE Chemical Properties

Boiling point:

271 °C

Density 

1.520 g/mL at 25 °C

refractive index 

n20/D 1.563

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Light yellow to Light orange

Water Solubility 

Not miscible in water.

BRN 

2641378

CAS DataBase Reference

35450-36-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

3

Hazard Note 

Toxic

HS Code 

29189900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

METHYL 2-BROMO-5-METHOXYBENZOATE Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

Methyl 2-bromo-5-methoxybenzoate is used as pharmaceutical intermediate.

Synthesis

To a stirred solution of 2-bromo-5-methoxybenzoic acid (5.0 g, 21.6 mmol) in methanol (80 mL) was slowly added concentrated hydrochloric acid (2 mL). The reaction mixture was heated to reflux and stirred continuously for 18 hours. Upon completion of the reaction, the solution was cooled to room temperature and the solvent was subsequently evaporated under reduced pressure. Water (100 mL) was added to the residue and extracted with ethyl acetate (2 x 100 mL). The organic phases were combined and washed with saturated aqueous sodium bicarbonate to remove unreacted acid. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to give methyl 2-bromo-5-methoxybenzoate as a light brown oil (4.50 g, 85% yield). The product was confirmed by NMR hydrogen spectrum (300 MHz, CDCl3): δH 7.53 (1H, d, J=8.8 Hz, 3-H), 7.32 (1H, d, J=3.0 Hz, 6-H), 6.89 (1H, dd, J=3.0, 8.8 Hz, 4-H), 3.94 (3H, s, ArOCH3), 3.82 (3H, s. CO2CH3). Infrared spectroscopy (thin-film method) showed characteristic absorption peaks: 2951, 1732 (C=O), 1592, 1472, 1433, 1289, 1250, 1227, 1099, 1017, 975, 823, 792 cm-1. Thin-layer chromatography (unfolding reagent: hexane-ethyl acetate, 5:1) showed Rf-value of 0.58. All the data are in agreement with the literature reports ( Barhate, NB; Gajare, AS; Wakharkar, RD; Bedekar, AV Tetrahedron 1999,55,11127-11142).

References

[1] Tetrahedron, 1998, vol. 54, # 37, p. 11209 - 11234
[2] Journal of Organic Chemistry, 2003, vol. 68, # 11, p. 4586 - 4589
[3] Patent: WO2012/102985, 2012, A1. Location in patent: Page/Page column 111
[4] Patent: WO2008/75048, 2008, A2. Location in patent: Page/Page column 64-65
[5] Tetrahedron, 1995, vol. 51, # 37, p. 10115 - 10124

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