Methyl chlorodifluoroacetate → 1-Tert-butyl-2-methoxy-5-(trifluoromethyl)-4-nitrobenzene

https://huagongshe.com/de/reaction/74008

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Methyl chlorodifluoroacetate	HCID 73935	—
Edukt	Potassium Bromide	HCID 253877	—
Edukt	Potassium Fluoride	HCID 522689	—
Edukt	1-Bromo-5-(tert-butyl)-4-methoxy-2-nitrobenzene	HCID 57470245	—
Katalysator	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Lösungsmittel	Water	HCID 962	—
Lösungsmittel	Dimethylformamide	HCID 6228	—
Produkt	1-Tert-butyl-2-methoxy-5-(trifluoromethyl)-4-nitrobenzene	HCID 57470246	61,6%

Reaktionsbedingungen

Temperatur	125 °C

Reaktionsschritte

A mixture of 1-tert-butyl-2-methoxy-5-bromo-4-nitrobenzene (867 mg, 3.0 mmol), KF (348 mg, 6 mmol), KBr (714 mg, 6 mmol), CuI (684 mg, 3.6 mmol), methyl chlorodifluoroacetate (2.2 mL, 21.0 mmol) in DMF (5 mL) was stirred at 125° C. in a sealed tube overnight, cooled to room temperature, diluted with water and extracted three times with EtOAc. The combined organic layers were washed with brine and dried over anhydrous MgSO4. After removal of the solvent, the residue was purified by column chromatography (0-5% EtOAc-Hexane) to yield 1-tert-butyl-2-methoxy-5-(trifluoromethyl)-4-nitrobenzene (512 mg, 61%). 1H NMR (400 MHz, CDCl3) δ 7.60 (s, 1H), 7.29 (s, 1H), 3.90 (s, 3H), 1.33 (s, 9H).

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08829204B2
Quelldatensatz	uspto-grants-2014_09
ORD ID	ord-e77fe0383fc346d59ce7a71dd0be2d9e
Quellennotiz	uspto-grants-2014_09