2,4-Difluorobenzaldehyde → (NE,R)-N-[(2,4-difluorophenyl)methylidene]-2-methylpropane-2-sulfinamide

Participants

Role	Name	HCID	Charge
Reactant	2,4-Difluorobenzaldehyde	HCID 73770	—
Reactant	Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)	HCID 466102	—
Reactant	tert-Butylsulfinamide, (R)-(+)-	HCID 10964479	—
Catalyst	Copper Sulfate	HCID 24462	—
Solvent	Dichloromethane	HCID 6344	—
Product	(NE,R)-N-[(2,4-difluorophenyl)methylidene]-2-methylpropane-2-sulfinamide	HCID 88931146	91.3%

Reaction Conditions

Temperature	37 °C

Reaction Steps

2,4-difluorobenzaldehyde (20-a, 10 g, 70.4 mmol) in dichloromethane (300 ml) were added (R)-2-methylpropane-2-sulfinamide (8.5 g, 70.4 mmol), PPTS (1.85 g, 7.4 mmol) and anhydrous CuSO4 (22.5 g, 0.14 mol). The resulting mixture was stirred at 37° C. overnight. The mixture was then filtrated and the filtrate was concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/ethyl acetate=8/1) to provide the product, 20-b, (15.77 g, 91%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09079930B2
Source dataset	uspto-grants-2015_07
ORD ID	ord-9e59dd3fd5d740cbacc7ed5dbe902389
Source note	uspto-grants-2015_07