Sodium Carbonate → 5-Ethyl-2-fluoro-biphenyl

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Phenylboronic Acid	HCID 66827	—
Reactant	2-Bromo-4-ethyl-1-fluorobenzene	HCID 18711874	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	Water 1,2-dimethoxyethane	HCID 18180031	—
Product	5-Ethyl-2-fluoro-biphenyl	HCID 21432918	—

Reaction Conditions

Temperature	150 °C

Reaction Steps

To a degassed mixture of Intermediate 228.1 (104 mg, 0.512 mmol), phenylboronic acid (94 mg, 0.768 mmol) and Na2CO3 (217 mg, 2.05 mmol) in 4 mL DME/H2O (3:1) was added Pd(PPh3)4 (59 mg, 0.051 mmol). The mixture was stirred at 150° C. for 5 min in a microwave oven, then was diluted with EtOAc, washed with water and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (100% hexanes) to afford Intermediate 228.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07576098B2
Source dataset	uspto-grants-2009_08
ORD ID	ord-f0ecc30fe858434dbd837f304c614d5a
Source note	uspto-grants-2009_08