Triphenylphosphine → tert-butyl [(1S)-2-(4-bromo-3,5-difluorophenoxy)-1-methylethyl]carbamate

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	Diisopropyl diazene-1,2-dicarboxylate	HCID 75555	—
Reactant	1,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate	HCID 7023103	—
Reactant	4-Bromo-3,5-difluorophenol	HCID 7172027	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	tert-butyl [(1S)-2-(4-bromo-3,5-difluorophenoxy)-1-methylethyl]carbamate	HCID 86666328	58.2%

Reaction Conditions

Temperature	60 °C

Reaction Steps

To a solution of 4-bromo-3,5-difluorophenol (5.0 g), tert-butyl [(1S)-2-hydroxy-1-methylethyl]carbamate (5 g) and triphenylphosphine (7.5 g) in THF (50 mL) was added diisopropyl azodicarboxylate (1.9 M in toluene, 14 mL) dropwise at room temperature. The reaction mixture was stirred at 60° C. overnight and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to afford the title compound (5.1 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08729102B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-24623d532f0e450686ee1f9d209ae015
Source note	uspto-grants-2014_05