tert-Butanol → 1,4-Bis(4-bromophenyl)-1,4-butanedione

HRID 1470920Notes

Reaction equation

HRID 1470920 reaction equation
C(NCC)C.CC(O)(C)C.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)=[O:14].[Br:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[CH:25][CH:24]=1>C1C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([C:13](=[O:14])[CH2:12][CH2:30][C:29]([C:26]2[CH:27]=[CH:28][C:23]([Br:22])=[CH:24][CH:25]=2)=[O:31])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 74544-Bromophenacyl bromideHCID 7466p-BromoacetophenoneHCID 8021Diethylamine

Product 1

HCID 2192171,4-Bis(4-bromophenyl)-1,4-butanedioneYield 39.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 241BenzeneSolvent

Procedure

To a solution of zinc(II) chloride (19.62 g, 144 mmol) in benzene (108 mL) were added diethylamine (11.16 mL, 108 mmol) and 2-methylpropan-2-ol (10.32 mL, 108 mmol) and the mixture was stirred at room temperature for 2 h. 2-bromo-1-(4-bromophenyl)ethanone (20.0 g, (72 mmol) and 1-(4-bromophenyl)ethanone (21.48 g, 108 mmol) were added in one portion, and the mixture was stirred overnight (18 h). Quenched with 5% H2SO4 (500 mL) and stirred vigorously to induce precipitation of the product, which was collected by vacuum filtration and washed with benzene, water, methanol, then dichloromethane, successively. The product was dried under vacuum to give the title compound as a white solid (11.15 g, 39.1% yield).

Workup

  1. stirringthe mixture was stirred overnight (18 h)
  2. customQuenched with 5% H2SO4 (500 mL)
  3. stirringstirred vigorously
  4. customprecipitation of the product, which
  5. filtrationwas collected by vacuum filtration
  6. washwashed with benzene, water, methanol
  7. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-464b7fb6507147bd980da0786e9b8d0c
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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