Bromofluoromethane (BFM) 

Valliscor Capabilities for Bromofluoromethane

Bromofluoromethane (BFM) is an important building block primarily used in the commercial manufacture of the APIs fulticasone propionate and fuliticasone furoate. Using proprietary technology, Valliscor manufactures kilogram to commercial scale quantities of BFM for the pharmaceutical industry at its Corvallis, Oregon production facility.  To find out more information about our offerings, please contact us at info@valliscor.com.

Alternate Names: BFM, bromofluoromethylene, CFC 31B1, R 31B1
Catalog #: VCBFM
CAS #: 373-52-4
Molecular Weight: 112.916
Density: 1.76 g/mL
Boiling Point: 20°C
1H NMR Spectra (CDCl3): 6.1 (d, J(F-H) = 48 Hz, 2H) ppm
13C NMR Spectra (CDCl3): 77.4 (d, J(C-F) = 247 Hz) ppm
19F NMR Spectra (CDCl3):  -163.5 (t, J = 48.9 Hz) ppm
IR Spectra: Mol. Phys. 2006 , 104, 3187-3192

Microwave Spectra: J. Mol. Spec 2007 , 241, 112-115

WikipediaLink: http://en.wikipedia.org/wiki/Bromofluoromethane

Material Safety Data Sheet (MSDS) / Safety Data Sheet (SDS): [DOWNLOAD]
Downloadable Flyer on Valliscor’s Bromofluoromethane (BFM) Capabilities: [DOWNLOAD]

Fluticasone and Related Examples

The fluoromethyl moiety has proven useful in a range of pharmaceutically relevant targets and agrochemically-significant compounds. One of the first examples of the use of bromofluoromethane in the synthesis of a commercial product is in the fluoromethylation of a thioacid to manufacture fluticasone propionate by Glaxo (J. Med. Chem. 1994, 37, 3717-3729) (Eq. 1).

Subsequently, bromofluoromethane has been shown to be generally useful in accessing other fluticasone-related molecules – including fluticasone furoate (PCT Int. Appl., WO2007114363 A2, 21 Dec, 2007) by GlaxoSmithKline (Eq. 2).

Other companies have demonstrated the utility of bromofluoromethane to construct related scaffolds including Chiesi Farmaceutici’s pyrrolidine-containing glucocortosteroids (PCT Int. Appl., WO2011095535 A2, 11 Aug, 2011) (Eq. 3) and biaryl ether-containing glucocorticoids from Pfizer (PCT Int. Appl., WO2010136940 A1, 2 Dec, 2010) (Eq. 4).

PET Imaging Examples

Bromofluoromethane (BFM) has also proven useful for accessing PET imaging molecules. BFM can be cross coupled with boronic esters to access fluoromethyl aromatic compounds (Bull. Chem. Soc. Jpn 2012, 85, 1233-1238) (Eq. 5). Additionally, alkylation using phenolic nucleophiles such as the protected tyrosine derivative shown below provides a PET imaging precursor in good yield (PCT Int. Appl., WO2013001088, 3 Jan 2013) (Eq. 6).

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