2-FLUORO-5-METHOXYBENZOIC ACID Chemical Properties

Melting point:

146-150

Boiling point:

302.7±22.0 °C(Predicted)

Density 

1.307

storage temp. 

Sealed in dry,Room Temperature

pka

3.15±0.10(Predicted)

Appearance

White to off-white Solid

CAS DataBase Reference

367-83-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36

Hazard Note 

Irritant

HS Code 

2918999090

2-FLUORO-5-METHOXYBENZOIC ACID Usage And Synthesis

Chemical Properties

Class white powder

Uses

2-Fluoro-5-methoxybenzoic acid is used as an organic chemical synthesis intermediate.

Synthesis

The general procedure for the synthesis of 2-fluoro-5-methoxybenzoic acid from 4-fluoroanisole and carbon dioxide was as follows: 1-fluoro-4-methoxybenzene (5 g, 39.6 mmol, 1.0 eq.) and PMDTA (7.56 g, 43.62 mmol, 1.1 eq.) were dissolved in anhydrous THF (100 mL) under nitrogen protection and cooled to -60 °C. A solution of s-BuLi (1.3 M, 36.6 mL, 47.5 mmol, 1.2 eq.) was added slowly over 1 hr. The reaction mixture continued to be stirred at -60 °C for 2 hours. Subsequently, carbon dioxide gas was passed into the solution for 1 hour. After completion of the reaction, the mixture was slowly warmed to room temperature, acidified with 1 M HCl solution and extracted with EtOAc. The organic phases were combined, washed sequentially with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (eluent: EtOAc/petroleum ether, gradient from 0:1 to 1:1) to afford 2-fluoro-5-methoxybenzoic acid as a yellow solid (5.4 g, 80% yield).LC-MS: m/z 171.1 [M+H]+, 193.0 [M+Na]+. 1H NMR (400 MHz, DMSO-d6) δ. 13.33 (s, 1H), 7.31 (m, 1H), 7.24 (m, 1H), 7.20-7.16 (m, 1H), 3.78 (s, 3H).

References

[1] Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1271 - 1275
[2] Patent: WO2013/37705, 2013, A2. Location in patent: Page/Page column 61; 62
[3] Patent: WO2004/14856, 2004, A1. Location in patent: Page 21
[4] Tetrahedron Letters, 1992, vol. 33, # 49, p. 7495 - 7498

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