tert-Butanol → HCID 12016671, compound

HRID 1294638Notes

Reaction equation

HRID 1294638 reaction equation
CC(O)(C)C.[K].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[C:10]([C:18](=O)[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH:9]=1>COCCOC>[Br:7][C:8]1[CH:9]=[C:10]2[C:11](=[CH:12][CH:13]=1)[NH:14][C:15](=[O:17])[CH:16]=[C:18]2[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 5462222PotassiumHCID 23248656HCID 23248656, compound

Product 1

HCID 12016671HCID 12016671, compoundYield 80.76%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Methyl-2-propanol, potassium salt (1.635 mol) was added portionwise at room temperature to a solution of intermediate 3 (0.328 mol) in 1,2-dimethoxyethane (1200 ml) and the mixture was stirred at room temperature for one night. The mixture was evaporated till dryness, the residue was poured into water and ice and decanted. The oily residue was taken up in DIPE, the precipitate was filtered off, washed with EtOAc, acetonitrile and diethyl ether and dried, yielding 88.6 g (80.76%) of 6-bromo-4-(3-chlorophenyl)-2(1H)-quinolinone (intermediate 4).

Workup

  1. customThe mixture was evaporated till dryness
  2. additionthe residue was poured into water and ice
  3. customdecanted
  4. filtrationthe precipitate was filtered off
  5. washwashed with EtOAc, acetonitrile and diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-c530054ca64740faa172abc73bf539b3
Source dataset
uspto-grants-2007_07
Patent number
US07241777B2

Reaction notes

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