4-Isopropylacetophenone → 2-Bromo-1-(4-(propan-2-yl)phenyl)ethan-1-one

HRID 2172145Notes

Reaction equation

HRID 2172145 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:12])=[O:11])=[CH:6][CH:5]=1)[CH3:3].[Br:13]Br>C(OCC)(=O)C>[Br:13][CH2:12][C:10]([C:7]1[CH:6]=[CH:5][C:4]([CH:2]([CH3:1])[CH3:3])=[CH:9][CH:8]=1)=[O:11]

Participants

4

Reactant 2

HCID 125784-IsopropylacetophenoneHCID 24408Bromine

Product 1

HCID 140427562-Bromo-1-(4-(propan-2-yl)phenyl)ethan-1-oneYield 66.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-isopropylacetophenone (65 g) in ethyl acetate (250 mL) is cooled to 0° C. and treated with bromine (65 g) dropwise. The mixture is stirred for 5 h, then quenched by the addition of water (250 mL). The phases are separated, and the aqueous layer is extracted with ethyl acetate. The organic phases are washed with satd. aq. NaHCO3 and brine, combined, dried over Na2SO4, filtered and evaporated to afford the product, 2-bromo-4′-isopropylacetophenone (64 g, 66%).

Workup

  1. customquenched by the addition of water (250 mL)
  2. customThe phases are separated
  3. extractionthe aqueous layer is extracted with ethyl acetate
  4. washThe organic phases are washed with satd
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-5c406c10b4f94b3ab03dc848c74a0922
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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