Water → 4-Fluoro-2-(3-furanyl)-6-methylphenol

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Furan-3-boronic acid	HCID 2734358	—
Reactant	2-bromo-4-fluoro-6-methylphenol	HCID 19810899	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	4-Fluoro-2-(3-furanyl)-6-methylphenol	HCID 90002199	41.6%

Reaction Conditions

Temperature	120 °C

Reaction Steps

2-bromo-4-fluoro-6-methylphenol (337 mg, 1.20 mmol), 3-furanylboronic acid (162 mg, 1.45 mmol), Pd(dppf)Cl2 (98.3 mg, 0.12 mmol) and sodium carbonate (383 mg, 3.61 mmol) were dissolved in DME:water=20 mL:10 mL, followed by stirring in microwave at 120° C. for 20 minutes. The reaction mixture was filtered through Celite. The filtrate was concentrated under reduced pressure, and purified by column chromatography (silica gel; hexane/ethyl acetate, 9/1) to obtain 4-fluoro-2-(furan-3-yl)-6-methylphenol (96 mg, 30%) as a yellow oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09447083B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-4af0792f705347d9a7e7ca3dc00e4a31
Source note	uspto-grants-2016_09