Water → 2-Bromo-1-(4-tert-butylphenyl)ethan-1-one

HRID 576059Notes

Reaction equation

HRID 576059 reaction equation
[BrH:1].Br.Br.N1CCCC1=O.[C:10]([C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].O>O1CCCC1>[Br:1][CH2:21][C:20]([C:17]1[CH:16]=[CH:15][C:14]([C:10]([CH3:13])([CH3:11])[CH3:12])=[CH:19][CH:18]=1)=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 13669p-tert-ButylacetophenoneHCID 20283272Pyrrolidone trihydrobromide

Product 1

HCID 23247702-Bromo-1-(4-tert-butylphenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Pyrrolidone trihydrobromide (3.27 g, 10.0 mmol) was added to a solution of 1-(4-tert-butylphenyl)ethanone obtained (1.61 g, 9.13 mmol) in tetrahydrofuran (30 mL) and the mixture was heated to an external temperature of 60° C. and stirred for 30 min. After cooling, water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate and then the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane only→hexane:ethyl acetate=9:1) to afford the title compound as a colorless oil (472 mg).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationthe desiccant was filtered off
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane only→hexane

Sources & evidence

ORD record
ord-f1f4f4e3c8d547a386e2a72372f8552e
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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