3-Bromo-5-(1,1-difluoro-ethyl)-pyridine

3-Bromo-5-(1,1-difluoro-ethyl)-pyridine Property

storage temp. 

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

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C7H6BrF2N/c1-7(9,10)5-2-6(8)4-11-3-5/h2-4H,1H3

InChIKey

WHDYQJPECGZSLP-UHFFFAOYSA-N

SMILES

C1=NC=C(C(F)(F)C)C=C1Br

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H320Causes eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-Bromo-5-(1,1-difluoro-ethyl)-pyridine Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 3-bromo-5-(1,1-difluoroethyl)pyridine from 3-acetyl-5-bromopyridine: 1-(5-bromopyridin-3-yl)ethanone (500 mg, 2.5 mmol) and bis(2-methoxyethyl)aminosulfur trifluoride (BAST, 2.2 g, 10 mmol) were dissolved in dichloromethane (8 mL) in an airtight tube at 60 C overnight. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding reagent ratio PE:EtOAc = 1:1) and after confirming the completion of the reaction, the reaction mixture was concentrated. The residue was purified by fast column chromatography (silica gel as stationary phase, eluent ratio PE:EtOAc = 1:1) to afford the target product 3-bromo-5-(1,1-difluoroethyl)pyridine (200 mg, 36% yield). Mass spectrometry (MS) analysis showed (M + 1) = 222/224.

References

[1] Patent: WO2014/418, 2014, A1. Location in patent: Page/Page column 56
[2] Patent: US2015/197511, 2015, A1. Location in patent: Paragraph 0275; 0276
[3] Patent: WO2015/138220, 2015, A1. Location in patent: Page/Page column 87