Phenacyl bromide → HCID 68285598, compound

HRID 1618889Notes

Reaction equation

HRID 1618889 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([OH:11])[CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(CC(=O)C(C)(C)C)(=O)C(C)(C)C.Br[CH2:32][C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34]>CN1CCCC1=O.[Cu]Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([O:11][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[C:33](=[O:34])[CH3:32])[CH:2]=1

Participants

7

Reactant 4

HCID 6259Phenacyl bromideHCID 10796Cesium carbonateHCID 113763-HydroxyquinolineHCID 707002,2,6,6-Tetramethyl-3,5-heptanedione

Product 1

HCID 68285598HCID 68285598, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

0.73 g of 3-quinolinol, 1.8 g of cesium carbonate, 0.18 g of dipivaloylmethane, 2.0 g of 2-bromoacetophenone, and 0.50 g of copper (I) chloride were dissolved in 10 ml of N-methylpyrrolidone, and the mixture was stirred for 3 hours at 130° C. The resultant was purified by silica gel column chromatography, and 0.82 g of 1-[2-(quinolin-3-yloxy)-phenyl]-ethanone (Compound Number 1) was obtained.

Workup

  1. customThe resultant was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f9b356bc1e5741bcaf480b69f25b8bee
Source dataset
uspto-grants-2014_07
Patent number
US08772200B2

Reaction notes

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