Hydrochloric Acid → HCID 18314753, compound

HRID 362569Notes

Reaction equation

HRID 362569 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH2:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:6]([CH3:8])[CH3:7].Br[C:16]([CH3:21])([CH3:20])[C:17](Br)=[O:18].Cl>C(Cl)Cl>[CH3:20][CH:16]1[CH2:21][C:13]2[C:12](=[CH:11][CH:10]=[C:9]([CH2:5][CH:6]([CH3:8])[CH3:7])[CH:14]=2)[C:17]1=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10870IsobutylbenzeneHCID 886852-Bromo-2-methylpropionyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18314753HCID 18314753, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17.3 g (125 mmol) of aluminum trichloride were added with ice cooling to a solution of 6.7 g (50 mmol) of isobutyl benzene in 30 ml of methylene chloride. 11.9 g (52 mmol) of 2-bromoisobutyryl bromide were subsequently added rapidly, and the mixture was refluxed for 15 hours. The reaction mixture was poured into 100 ml of ice water, 25 ml of conc. aqueous HCl were added, and the mixture was extracted 3 times with 50 ml of diethyl ether in each case. The combined organic phases were washed with 50 ml each of saturated aqueous NaHCO3 solution and NaCl solution and dried (MgSO4). After removal of the solvent on a rotary evaporator, the crude product was chromatographed on 100 g of silica gel (hexane/methylene chloride 1:1), giving 8.4 g (83%) of 1 as a colorless oil.

Workup

  1. temperaturethe mixture was refluxed for 15 hours
  2. additionwere added
  3. extractionthe mixture was extracted 3 times with 50 ml of diethyl ether in each case
  4. washThe combined organic phases were washed with 50 ml each of saturated aqueous NaHCO3 solution and NaCl solution
  5. dry with materialdried (MgSO4)
  6. customAfter removal of the solvent
  7. customon a rotary evaporator
  8. customthe crude product was chromatographed on 100 g of silica gel (hexane/methylene chloride 1:1)

Sources & evidence

ORD record
ord-fdd05924f500454ab691b6a7d5cfae8e
Source dataset
uspto-grants-1999_02
Patent number
US05869584

Reaction notes

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