Dimethylformamide → 5-Bromo-3,3,7-trimethyl-2,3-dihydro-benzofuran

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Potassium Acetate	HCID 517044	—
Reactant	2,4-Dibromo-6-methylphenyl 2-methylprop-2-en-1-yl ether	HCID 15454074	—
Reactant	HCID 178526064	HCID 178526064	—
Catalyst	Tetraethylammonium Chloride	HCID 5946	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Product	5-Bromo-3,3,7-trimethyl-2,3-dihydro-benzofuran	HCID 15454076	70%

Reaction Conditions

Temperature	75 °C

Reaction Steps

To a nitrogen flushed 100 mL round bottom flask were added 2,4-dibromo-6-methylphenyl 2-methylprop-2-en-1-yl ether (710 mg, 2.22 mmol), Pd(dppf)Cl2 (36 mg, 0.044 mmol), Et4NCl (490 mg, 2.66 mmol), KOAc (544 mg, 5.55 mmol), HCO2Na (181 mg, 2.66 mmol), DMF (20 mL) and water (1 mL). The reaction mixture was heated at 75° C. overnight. After cooling to room temperature, it was diluted with water and extracted with EtOAc/hexanes (1:3). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified on a silica gel column eluting with a gradient of 100% hexanes to 10% EtOAc/hexanes to give the title intermediate (110 mg, 70% purity) as light yellow liquid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08742110B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-9361579a0c8e451a83a487b13e3e2b32
Source note	uspto-grants-2014_06