Potassium Carbonate → 4-Bromo-2-tert-butyl-difluoromethoxy-benzene

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Acetic acid, 2-chloro-2,2-difluoro-, ethyl ester	HCID 67843	—
Reactant	4-Bromo-2-tert-butylphenol	HCID 97068	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	4-Bromo-2-tert-butyl-difluoromethoxy-benzene	HCID 67286430	33.2%

Reaction Conditions

Temperature	80 °C

Reaction Steps

step 1—To a mixture of 4-bromo-2-tert-butyl-phenol (640 mg, 2.795 mmol) and potassium carbonate (1.20 g, 8.682 mmol) in DMF (8 mL) was added ethyl chlorodifluoroacetate (1.1 mL, 8.687 mmol). The reaction was heated to 80° C. overnight then cooled to RT, and diluted with EtOAc and water. The organic layer was washed with water, with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 column eluting with hexane to afford 259 mg (33%) of 4-bromo-2-tert-butyl-difluoromethoxy-benzene (20) as a colorless oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08273773B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-ffe164955dc345f2b337eead1082d239
Source note	uspto-grants-2012_09