Potassium Acetate → 2-Chloro-3-(2,2,4-trimethyl-1,2-dihydroquinolin-6-yl)-phenol

Participants

Role	Name	HCID	Charge
Reactant	Potassium Acetate	HCID 517044	—
Reactant	2-Chloro-3-iodophenol	HCID 11379814	—
Reactant	2,2,4-Trimethyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2-dihydroquinoline	HCID 22566530	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	2-Chloro-3-(2,2,4-trimethyl-1,2-dihydroquinolin-6-yl)-phenol	HCID 22566541	81%

Reaction Steps

2,2,4-Trimethyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2-dihydroquinoline (308 mg) and 393 mg of 2-chloro-3-iodophenol were coupled using of 100 mg of PdCl2(dppf) and 300 mg of KOAc to give 250 mg of 2-chloro-3-(2,2,4-trimethyl-1,2-dihydroquinolin-6-yl)-phenol. Using the procedures described in Example 7, this (85 mg) was reacted with NBS to give 56 mg of 3-(4-bromomethyl-2,2-dimethyl-1,2-dihydroquinolin-6-yl)-2-chlorophenol. The product (50 mg) was coupled with 0.04 mL of 2-phenylethanethiol to give 40 mg of the title compound as an oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06858627B2
Source dataset	uspto-grants-2005_02
ORD ID	ord-c2ec3a25f4384f3089531b8b42fa06df
Source note	uspto-grants-2005_02