4-Bromo-2,6-difluoroaniline

Description

4-Bromo-2,6-difluoroaniline is a polyfunctional aniline derivative bearing a bromine atom at the para-position and two fluorine atoms at the ortho-positions. Its functional groups render this compound relatively reactive, enabling participation in substitution, displacement, and condensation coupling reaction systems. It finds extensive application within the field of organic synthesis. Furthermore, conjugated quasi-planar triphenylamines synthesised from 4-bromo-2,6-difluoroaniline serve as hole-transporting materials in perovskite solar cells and organic light-emitting diodes (OLEDs).

Chemical Properties

Off-white crystalline

Uses

4-Bromo-2,6-difluoroaniline was used in synthesis of:

• ammonium 5-bromo-7-fluorobenzo-2-oxa-1,3-diazole-4-sulphonate, fluorogenic derivatizating reagent for the determination of aminothiols by HPLC
• olefin tolanes
• 1-(4-amino-3,5-difluoro)-2-(4-butyloxyphenyl)ethyne
• 4′′-n-butyloxy-3,5-difluoroterphenyl-4-amine
• 4-(3-methylbut-1-yn-3-ol)-2,6-difluoroaniline

Uses

4-Bromo-2,6-difluoroaniline is used in the preparation of potent, VEGF receptor tyrosine kinase inhibitors.

Synthesis

5509-65-9

67567-26-4

b) Preparation of Intermediate 2: Dissolve 2,6-difluoroaniline (3.0 g, 22.56 mmol) in acetic acid (10 mL). Bromine (1.2 mL) was slowly added dropwise to the above solution. The reaction mixture was stirred at room temperature for 15 minutes. After the reaction was completed, the solvent was evaporated under reduced pressure. The residue was neutralized with aqueous sodium carbonate and the aqueous phase was subsequently extracted with dichloromethane. The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give Intermediate 2 in 92% yield.

References

[1] Angewandte Chemie - International Edition, 2016, vol. 55, # 4, p. 1544 - 1547
[2] Angew. Chem., 2016, vol. 128, # 4, p. 1569 - 1573,5
[3] Journal of Materials Chemistry C, 2016, vol. 4, # 23, p. 5326 - 5333
[4] Patent: WO2006/15985, 2006, A1. Location in patent: Page/Page column 54
[5] Patent: US6716491, 2004, B2