Diethyl Ether → Tert-butyl 2-(3-fluoro-4-(2-fluoropyridin-4-yl)phenyl)acetate

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Diethyl Ether	HCID 3283	—
Edukt	4-(4-Bromo-2-fluorophenyl)-2-fluoropyridine	HCID 58447799	—
Edukt	HCID 178451183	HCID 178451183	—
Katalysator	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Katalysator	Ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene	HCID 129828017	—
Lösungsmittel	Tetrahydrofuran	HCID 8028	—
Produkt	Tert-butyl 2-(3-fluoro-4-(2-fluoropyridin-4-yl)phenyl)acetate	HCID 58447777	—

Reaktionsbedingungen

Temperatur	100 °C

Reaktionsschritte

To a sealed tube were added 4-(4-bromo-2-fluorophenyl)-2-fluoropyridine 207-3 (210 mg, 0.76 mmol), 0.5 M (2-tert-butoxy-2-oxoethyl) zinc(II) chloride 86-5 in ether (2.3 mL, 1.14 mmol), Pd(dba)2 (22 mg, 0.04 mmol), Q-phos (54 mg, 0.07 mmol) and THF (5 mL). The reaction mixture was bubbled with nitrogen for 1 minute and stirred at 100° C. for 1 hour. After cooling to room temperature, all the solvents were evaporated and the residue was redissolved in ethyl acetate, washed with water and brine, dried over Na2SO4 and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography and eluted with 20% ethyl acetate in hexane to give tert-butyl 2-(3-fluoro-4-(2-fluoropyridin-4-yl)phenyl)acetate 207-5. MS m/z 306.2 (M+1).

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US09238646B2
Quelldatensatz	uspto-grants-2016_01
ORD ID	ord-54ec58fd4c9749f4b242b5dfae2c4dd4
Quellennotiz	uspto-grants-2016_01