Potassium tert-butoxide → HCID 118324132, compound

HRID 1778257Notes

Reaction equation

HRID 1778257 reaction equation
Br[C:2]1[CH:11]=[C:10]([Br:12])[C:9]2[C:4](=[C:5]([Br:22])[CH:6]=[C:7]([C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[O:14])[CH:8]=2)[N:3]=1.[CH3:23][C:24]([O-:27])([CH3:26])[CH3:25].[K+]>C1(C)C=CC=CC=1.[Cl-].[Na+]>[Br:12][C:10]1[C:9]2[C:4](=[C:5]([Br:22])[CH:6]=[C:7]([C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[O:14])[CH:8]=2)[N:3]=[C:2]([O:27][C:24]([CH3:26])([CH3:25])[CH3:23])[CH:11]=1

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 118324040HCID 118324040, compound

Product 1

HCID 118324132HCID 118324132, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 5234Sodium ChlorideSolvent

Conditions

Temperature
65 °C

Procedure

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2,4,8-tribromo-6-[(4-chlorophenyl)carbonyl]quinoline (1.0 g, 1.98 mmol, 1.00 equip) in toluene (30 mL), and KOt-Bu (2.18 mL, 1.10 equip). The resulting solution was stirred for 1.5 h at 65° C. The resulting solution was diluted with saturated sodium chloride (50 mL). The resulting solution was extracted with ethyl acetate (2×100 mL) and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (5:95) to yield 4,8-dibromo-2-(tert-butoxy)-6-[(4-chlorophenyl)carbonyl]quinoline as a yellow solid. LCMS (ES, m/z) 498 [M+H]+

Workup

  1. customInto a 100-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. extractionThe resulting solution was extracted with ethyl acetate (2×100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe solids were filtered out
  6. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-a6a3a739b21a437281e60b913de41a74
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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