Water → HCID 118323959, compound

HRID 1778214Notes

Reaction equation

HRID 1778214 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[C:15](Br)[CH:14]=[C:13]3[Br:21])=[O:9])=[CH:4][CH:3]=1.[OH2:22]>C1(C)C=CC=CC=1.CCOC(C)=O>[Br:21][C:13]1[C:12]2[C:17](=[CH:18][CH:19]=[C:10]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:9])[CH:11]=2)[N:16]=[C:15]([O:22][C:5]([CH3:8])([CH3:6])[CH3:4])[CH:14]=1

Participants

5

Reactant 2

HCID 962WaterHCID 118324146(4-Chlorophenyl)(2,4-dibromoquinolin-6-yl)methanone

Product 1

HCID 118323959HCID 118323959, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of (4-chlorophenyl)(2,4-dibromoquinolin-6-yl)methanone (5 g) and KOBut (1.1 eq. 12.93 mmol) in dry toluene (60 mL) was heated at 70° C. for 2 hr. and then cooled to room temperature. The reaction was diluted with EtOAc and water. The aqueous layer was extracted with ethyl acetate. The organics were combined and then washed with water, concentrated and subjected to chromatography (5-15% EtOAc/hexanes silica column) to yield (4-bromo-2-(tert-butoxy)quinolin-6-yl)(4-chlorophenyl)methanone.

Workup

  1. temperatureand then cooled to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washwashed with water
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-689d515bac0944298b9f99400c1c679f
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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