4-Methylbenzenethiol → HCID 66736270, compound

Participants

Role	Name	HCID	Charge
Reactant	4-Methylbenzenethiol	HCID 7811	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	HCID 66736357	HCID 66736357	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 66736270	HCID 66736270	53.9%

Reaction Steps

A solution of 4-[2-(4′-bromo-2′-fluorobiphenyl-4-yl)ethyl]-4-di(tert-butyl)phosphoryloxymethyl-2-methyl-2-oxazoline (210 mg) of Example 23, (23-2), 4-methylbenzenethiol (49 mg), diisopropylethylamine (93 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (18.6 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (21.4 mg) in 1,4-dioxane (2 mL) was heated under reflux for 9 hr under a nitrogen atmosphere. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (122 mg) as a pale-yellow oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08114902B2
Source dataset	uspto-grants-2012_02
ORD ID	ord-a89ef6da43be49ba8c0af48b9650dec3
Source note	uspto-grants-2012_02