4-Chloro-4'-isopropylbutyrophenone → 1-Butanone, 1-[4-(1-bromo-1-methylethyl)phenyl]-4-chloro-

HRID 1857841Notes

Reaction equation

HRID 1857841 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=1)=[O:6].[Br:16]([O-])(=O)=O.[Na+].[Br-].[Na+]>C(Cl)Cl.O.S(S([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+]>[Br:16][C:13]([C:10]1[CH:9]=[CH:8][C:7]([C:5](=[O:6])[CH2:4][CH2:3][CH2:2][Cl:1])=[CH:12][CH:11]=1)([CH3:15])[CH3:14]

Participants

7

Reactant 3

HCID 987444-Chloro-4'-isopropylbutyrophenoneHCID 253881Sodium BromideHCID 23668195Sodium Bromate

Product 1

HCID 100635791-Butanone, 1-[4-(1-bromo-1-methylethyl)phenyl]-4-chloro-Yield 281.5%

Reagents, catalysts & solvents 3

HCID 146045Sodium dithionateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

Dissolve 4-chloro-1-(4-isopropyl-phenyl)-butan-1-one (74.7 g, 333 mmol) in methylene chloride (250 mL) and add sodium bromate (17.6 g, 117 mmol) in water (75 mL) in a three-necked Morton flask equipped with an overhead stirrer. Cool the solution to 10° C. and irradiate with two 150 W incandescent flood lamps. Add, by dropwise addition, a solution of sodium bromide (24 g, 233 mmol) and stir for 2 hours. Illuminate for another 30 minutes, add sodium dithionate (2.0 g), separate the organic phase, dry (MgSO4) and evaporate the solvent in vacuo to give the title compound (100 g, 99%).

Workup

  1. customequipped with an overhead stirrer
  2. customirradiate with two 150 W incandescent flood lamps
  3. additionAdd, by dropwise addition
  4. customIlluminate for another 30 minutes
  5. customseparate the organic phase
  6. dry with materialdry (MgSO4)
  7. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-e4625cfbec054fb29c75d16fe941f212
Source dataset
uspto-grants-2000_11
Patent number
US06147216

Reaction notes

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