TERT-BUTYL 5-BROMOPYRIDINE-2-CARBOXYLATE 98 Chemical Properties

Melting point:

92-94

Boiling point:

318℃

Density 

1.385

Flash point:

146℃

storage temp. 

Inert atmosphere,Room Temperature

pka

-0.52±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C10H12BrNO2/c1-10(2,3)14-9(13)8-5-4-7(11)6-12-8/h4-6H,1-3H3

InChIKey

GBAJDPJECJPPSP-UHFFFAOYSA-N

SMILES

C1(C(OC(C)(C)C)=O)=NC=C(Br)C=C1

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant/Keep Cold

HS Code 

2933399990

TERT-BUTYL 5-BROMOPYRIDINE-2-CARBOXYLATE 98 Usage And Synthesis

Synthesis

The general procedure for the synthesis of tert-butyl 5-bromopyridine-2-carboxylate from 2-carboxylic acid-5-bromopyridine and tert-butanol was as follows: 2-carboxylic acid-5-bromopyridine (118 mg, 0.58 mmol) was mixed with pyridine (0.3 mL, 0.39 mmol) and tert-butanol (1 mL), and p-toluenesulfonyl chloride (262 mg, 1.38 mmol) was subsequently added. The reaction mixture was stirred at 40°C for 10 minutes and then continued to stir at room temperature for 2 hours. After the reaction was completed, saturated sodium bicarbonate solution (4 mL) was added and stirred for 5 minutes. Then diethyl ether was added and the two-phase mixture was stirred for 10 minutes. The organic layer was separated, washed with brine, dried with anhydrous magnesium sulfate and subsequently concentrated under reduced pressure. The residue was purified by silica gel column chromatography with the eluent being pentane: ethyl acetate (100:0 to 80:20) to afford tert-butyl 5-bromopyridine-2-carboxylate as a colorless solid in 73% (110 mg) yield. The product was confirmed by 1H-NMR (CDCl3, 400 MHz): δ 1.65 (s, 9H), 7.95 (m, 2H), 8.88 (m, 1H). The mass spectrum (ES+) showed m/z 539 [M2Na]+.

References

[1] Patent: EP1595881, 2005, A1. Location in patent: Page/Page column 62
[2] Patent: WO2005/14571, 2005, A1. Location in patent: Page/Page column 27
[3] Patent: WO2006/29906, 2006, A1. Location in patent: Page/Page column 16-17
[4] Patent: WO2012/143599, 2012, A1. Location in patent: Page/Page column 47-48

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