2-CHLORO-3-FLUOROBENZOIC ACID Chemical Properties

Melting point:

171 °C

Boiling point:

279.5±20.0 °C(Predicted)

Density 

1.477±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

2.56±0.25(Predicted)

color 

White to Almost white

CAS DataBase Reference

102940-86-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39-37

HazardClass 

IRRITANT

HS Code 

29163990

2-CHLORO-3-FLUOROBENZOIC ACID Usage And Synthesis

Chemical Properties

White powder

Uses

2-Chloro-3-fluorobenzoic Acid is a useful synthetic intermediate. It can be used to synthesize aminobenzhydrol derivatives containing pendant cyclic amines as inhibitors of squalene synthase and cholesterol synthase. It can also be used to prepare aryl aminopyrazole benzamides as oral non-steroidal selective glucocorticoid receptor agonists.

Synthesis

General procedure for the synthesis of 2-chloro-3-fluorobenzoic acid from m-fluorobenzoic acid: 1. 3-Fluorobenzoic acid (4.02 g, 28.71 mmol) was dissolved in 20 mL of tetrahydrofuran (THF) to prepare a solution. 2. the above solution was slowly added dropwise to a suspension containing tetramethylene diamine (TMEDA) (10.00 mL, 66.3 mmol) and 1.3 M sec-butyllithium (sec-BuLi) (48 mL, 62.4 mmol) at -90 °C. the solution was then dissolved in 20 mL of tetrahydrofuran (THF) to form a solution. 3. 50 mL of THF was added to dilute the reaction mixture, maintaining the temperature at -90°C with continuous stirring for 35 minutes. 4. The reaction mixture was slowly warmed to -78°C followed by the addition of a solution of hexachloroethane (27.0 g, 113.9 mmol) in 50 mL of THF. 5. After the reaction had proceeded for 20 h, the reaction was quenched with water and the reaction mixture was diluted with ether. 6. The pH of the reaction mixture was adjusted to 1-2 using concentrated hydrochloric acid (HCl) to promote stratification. 7. The organic layer was separated, washed sequentially with water and brine, then dried and concentrated to give 30.4 g of crude product (tan solid). 8. The crude product was washed with hexane to yield 3.728 g (74% yield) of the target product 2-chloro-3-fluorobenzoic acid (1a) as a light tan solid. Mass spectrometry (MS) analysis showed m/z 175.2 (M + H).

References

[1] Patent: WO2004/39775, 2004, A2. Location in patent: Page 12
[2] Patent: WO2009/39091, 2009, A1. Location in patent: Page/Page column 13
[3] Patent: WO2007/150015, 2007, A2. Location in patent: Page/Page column 5
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 10, p. 1265 - 1272
[5] Bulletin de la Societe Chimique de France, 1996, vol. 133, # 2, p. 133 - 141

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