4-Bromo-tetrahydropyran

Chemical Properties

Light yellow liquid

Uses

4-Bromo-tetrahydropyran is a useful reactant in organic synthesis.

Uses

Reactant for:

• Nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents
• Preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans
• Preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes
• Preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity
• Preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives
• Synthesis of gephyrotoxin via the Schmidt reaction

Synthesis

General procedure for the synthesis of 4-bromotetrahydropyran from tetrahydropyran-4-ol: A. Preparation of 4-bromotetrahydropyran. Tetrahydropyran-4-ol (1.0 g, 10 mmol), carbon tetrabromide (3.6 g, 11 mmol) and triphenylphosphine (3.1 g, 12 mmol) were dissolved in dichloromethane (25 mL) and the reaction was stirred at room temperature overnight. Upon completion of the reaction, the crude reaction mixture was concentrated and subsequently purified by rapid chromatography on silica gel (eluent ratio ethyl acetate:hexane = 1:20) to afford the target product 4-bromotetrahydropyran as a colorless oil (1.4 g, 87% yield).

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 7, p. 2780 - 2789
[2] Patent: WO2005/9973, 2005, A1. Location in patent: Page/Page column 85; 86
[3] Angewandte Chemie - International Edition, 2007, vol. 46, # 19, p. 3556 - 3558
[4] Justus Liebigs Annalen der Chemie, 1937, vol. 532, p. 80
[5] Chem.Abstr., 1940, p. 4396