Sulfuric Acid → HCID 57423673, compound

HRID 1725160Notes

Reaction equation

HRID 1725160 reaction equation
C(NCC)C.C(O)(C)(C)C.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=1.Br[CH2:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24].S(=O)(=O)(O)O>C1(C)C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH2:19][CH2:22][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])=[CH:14][CH:13]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 6259Phenacyl bromideHCID 6386tert-ButanolHCID 8021DiethylamineHCID 98284'-Fluoroacetophenone

Product 1

HCID 57423673HCID 57423673, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalyst2×HCID 1140TolueneSolvent

Procedure

Diethylamine (55 mmol, 5.69 mL) and t-Butanol (55 mmol, 5.26 mL) are added to a stirred solution of Zinc Chloride (74 mmol, 10 g) in anhydrous toluene (100 mL). After two hours of stirring at room temperature, Zinc Chloride is completely dissolved. 1-(4-Fluorophenyl)-ethanone (40 mmol, 4.90 mL) is added, followed by the addition of bromoacetophenone (37 mmol, 7.4 g). The reaction is allowed to stir at room temperature for 3 days. A 5% aqueous solution of sulfuric acid (75 mL) is added and the organic phase is separated from the aqueous phase. The aqueous phase is extracted with Ethyl Acetate (50 mL) and the two organic phases are combined. The organic phase is dried with Sodium Sulfate, filtered and concentrated to give 1-(4-fluoro-phenyl)-4-phenyl-butane-1,4-dione (5.2 g) confirmed by LCMS, as a white solid.

Workup

  1. stirringto stir at room temperature for 3 days
  2. customthe organic phase is separated from the aqueous phase
  3. extractionThe aqueous phase is extracted with Ethyl Acetate (50 mL)
  4. dry with materialThe organic phase is dried with Sodium Sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8548ae5614ad461b9491f897205e9e63
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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