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

HRID 25821Notes

Reaction equation

HRID 25821 reaction equation
[CH3:1][C:2]1([CH3:22])[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7](B3OC(C)(C)C(C)(C)O3)[CH:8]=2)[NH:3]1.[Cl:23][C:24]1[C:29](I)=[CH:28][CH:27]=[CH:26][C:25]=1[OH:31].CC([O-])=O.[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:23][C:24]1[C:29]([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[NH:3][C:2]([CH3:1])([CH3:22])[CH:11]=[C:10]3[CH3:12])=[CH:28][CH:27]=[CH:26][C:25]=1[OH:31]

Participants

5

Reactant 3

HCID 517044Potassium AcetateHCID 113798142-Chloro-3-iodophenolHCID 225665302,2,4-Trimethyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2-dihydroquinoline

Product 1

HCID 225665412-Chloro-3-(2,2,4-trimethyl-1,2-dihydroquinolin-6-yl)-phenolYield 81%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

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.

Sources & evidence

ORD record
ord-c2ec3a25f4384f3089531b8b42fa06df
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Reaction notes

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