Ethyl 6-bromopicolinate Chemical Properties

Melting point:

41-42°C

Boiling point:

302.7±22.0 °C(Predicted)

Density 

1.501±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

-0.89±0.10(Predicted)

form 

solid

color 

Off-white

CAS DataBase Reference

21190-88-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

HS Code 

2933399990

Ethyl 6-bromopicolinate Usage And Synthesis

Uses

ethyl 6-bromopicolinate is a model compound for the preliminary screening of dimerization reaction.

Preparation

Ethyl 6-bromopicolinate was prepared by monolithiation of 2,6-dibromopyridine followed by a reaction with ethyl formate and subsequently by a reaction with iodine in ethanol (Scheme 57). This three-step procedure furnished the required ethyl 6-bromopicolinate in 45% yield.

Synthesis of Ethyl 6-bromopicolinate

Synthesis

At -78 °C, n-butyllithium (n-BuLi, 1.67 M hexane solution, 1.32 mL, 2.2 mmol) was slowly added dropwise to a tetrahydrofuran (THF, 3 mL) solution of 2,6-dibromopyridine (383 mg, 2.0 mmol) and the dropwise process was continued for 30 min. Subsequently, ethyl formate (1.6 mL, 20 mmol) was added to the reaction mixture and stirring was continued at -78 °C. After maintaining this temperature for 3 hours, iodine (I2, 1523 mg, 6 mmol), potassium carbonate (K2CO3, 1382 mg, 10 mmol), and ethanol (EtOH, 3 mL) were added sequentially, and then the mixture was warmed to room temperature and stirred for 14 hours. After completion of the reaction, the reaction was quenched with saturated aqueous sodium sulfite (Na2SO3) (5 mL) and extracted with chloroform (CHCl3, 3 x 20 mL). The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated to give ethyl 6-bromopyridine-2-carboxylate in 77% yield. If necessary, the product could be further purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9:1) to obtain ethyl 6-bromopyridine-2-carboxylate as colorless oil.

References

[1] Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709

Ethyl 6-bromopicolinate(21190-88-5)Related Product Information

• 6-Bromonicotinic acid
• (6-BROMO-PYRIDIN-3-YL)-METHANOL
• 6-FLUORONICOTINIC ACID METHYL ESTER
• 6-Bromopyridine-2-carbaldehyde
• 2-Bromo-6-pyridinemethanol
• Ethyl 6-bromopicolinate
• Ethyl formate
• 3-AMINO-6-BROMOPYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER
• 5-Bromopyridine-3-carboxylic acid ethyl ester
• 3-BROMOPYRIDINE-4-CARBOXYLIC ACID ETHYL ESTER
• 5-BROMOPYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER
• 6-BROMOPYRIDINE-2-ETHYL FORMATE
• ethyl 5-bromopyridine-2-carboxylate
• 6-BROMOPYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER
• 6-Bromopicolinic acid
• 6-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER