5-BROMO-2-BROMOMETHYL-BENZOIC ACID METHYL ESTER Chemical Properties

Boiling point:

349.7±32.0 °C(Predicted)

Density 

1.780±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

liquid

color 

Yellow

InChI

InChI=1S/C9H8Br2O2/c1-13-9(12)8-4-7(11)3-2-6(8)5-10/h2-4H,5H2,1H3

InChIKey

UVIJBFVFEGZZLQ-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC(Br)=CC=C1CBr

Safety Information

HS Code 

2916310090

5-BROMO-2-BROMOMETHYL-BENZOIC ACID METHYL ESTER Usage And Synthesis

Uses

Methyl 5-bromo-2-bromotoluate is a carboxylic acid ester derivative and can be used as a pharmaceutical intermediate.

Synthesis

Methyl 5-bromo-2-methylbenzoate (1 g, 4.4 mmol) was added to N-bromosuccinimide (0.80 g, 4.4 mmol) and benzoyl peroxide (56 mg, 0.23 mmol) in carbon tetrachloride (20 mL). The reaction mixture was stirred at 85°C for 2 hours. Upon completion of the reaction, the mixture was filtered through a silica gel pad and subsequently concentrated under vacuum to afford the target product methyl 5-bromo-2-bromomethylbenzoate (1.3 g, 97% yield). The structure of the product was confirmed by ESI-MS, m/z: 306.0 [M + H]+.

References

[1] Patent: WO2018/68017, 2018, A1. Location in patent: Page/Page column 144
[2] Organic and Biomolecular Chemistry, 2017, vol. 15, # 48, p. 10172 - 10183
[3] Patent: WO2014/76104, 2014, A1. Location in patent: Page/Page column 63
[4] Patent: CN107474006, 2017, A. Location in patent: Paragraph 0050; 0051; 0053; 0056-0057; 0059; 0062-0063; 0065
[5] Patent: WO2008/23161, 2008, A1. Location in patent: Page/Page column 116-117

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