Sulfuric Acid → HCID 58226578, compound

HRID 1470939Notes

Reaction equation

HRID 1470939 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].[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[CH:27][CH:26]=1)([O-:24])=[O:23].S(=O)(=O)(O)O>[Cl-].[Zn+2].[Cl-].C1C=CC=CC=1>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([C:13](=[O:14])[CH2:12][CH2:32][C:31]([C:28]2[CH:27]=[CH:26][C:25]([N+:22]([O-:24])=[O:23])=[CH:30][CH:29]=2)=[O:33])=[CH:16][CH:17]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 74544-Bromophenacyl bromideHCID 7487p-NitroacetophenoneHCID 8021Diethylamine

Product 1

HCID 58226578HCID 58226578, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 241BenzeneSolvent

Procedure

Added benzene (108 mL) to anhydrous zinc(II) chloride (19.62 g, 144 mmol), followed by the addition of diethylamine (11.16 mL, 108 mmol) and 2-methylpropan-2-ol (10.32 mL, 108 mmol) and stirred at room temperature for 2 h. Added 2-bromo-1-(4-bromophenyl)ethanone (20 g, 72.0 mmol) and 1-(4-nitrophenyl)ethanone (17.83 g, 108 mmol) together and stirred mixture for 18 h. Added 5% aq. sulfuric acid (50 mL) and stirred vigorously, then the product was collected by filtration, rinsed with benzene, water, methanol, dichloromethane and dried under vacuum to provide the product (15.0 g, 58% yield, colorless powder).

Workup

  1. stirringstirred vigorously
  2. filtrationthe product was collected by filtration
  3. washrinsed with benzene, water, methanol, dichloromethane
  4. customdried under vacuum
  5. customto provide the product (15.0 g, 58% yield, colorless powder)

Sources & evidence

ORD record
ord-95c7d3c20c5743aeae7774f08cda6f21
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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