Cesium carbonate → 1-Bromo-4-chloro-2-(difluoromethoxy)benzene

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Sodium chlorodifluoroacetate	HCID 2734985	—
Reactant	2-Bromo-5-chlorophenol	HCID 13284272	—
Solvent	Water	HCID 962	—
Solvent	tert-Butyl methyl ether	HCID 15413	—
Solvent	N,N-Dimethylformamide--water (1/1)	HCID 21962138	—
Product	1-Bromo-4-chloro-2-(difluoromethoxy)benzene	HCID 22295381	98%

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a solution of 2-bromo-5-chlorophenol (1 g, 4.8 mmol) in DMF/water (45 mL/5 mL) was added sodium chlorodifluoroacetate (1.95 g, 12.0 mmol) and cesium carbonate (3.14 g, 9.64 mmol), and the reaction mixture was heated to 100° C. for 4 hours. The reaction mixture was cooled and diluted with TBME (20 mL) and water (20 mL). The organic layer was collected, washed with saturated aqueous NaHCO3 solution, brine, dried over Na2SO4 and concentrated in vacuo to afford the title compound (1.21 g, 98%), which was used without further purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09067922B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-745b371fd6164f158f4241b233667c74
Source note	uspto-grants-2015_06