2-Bromo-2-methylpropionyl bromide → 7-Bromo-5-isopropyl-2-methyl-1-indanone

HRID 269456

Reaction equation

HRID 269456 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].Br[C:6]([CH3:11])([CH3:10])[C:7](Br)=[O:8].[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[CH:14]=1>ClCCl>[Br:12][C:13]1[CH:14]=[C:15]([CH:19]([CH3:21])[CH3:20])[CH:16]=[C:17]2[C:18]=1[C:7](=[O:8])[CH:6]([CH3:11])[CH2:10]2

Participants

5

Reactant 3

HCID 886852-Bromo-2-methylpropionyl bromideHCID 1384991-Bromo-3-isopropylbenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 121624887-Bromo-5-isopropyl-2-methyl-1-indanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-10 °C

Procedure

To a mixture of 34.9 g (0.26 mol) of AlCl3 and 350 ml of dichloromethane, a solution of 50.9 g (0.22 mol) of 2-bromo-2-methylpropanoyl bromide in 120 ml of dichloromethane was added dropwise, while vigorously stirring, at −10° C. Then, a solution of 40.0 g (0.20 mol) of 1-bromo-3-isopropylbenzene in 70 ml of dichloromethane was added dropwise at this temperature. The resulting mixture was refluxed for 12 h and then poured onto 2000 cm3 of ice. The organic product was extracted with 4×300 ml of dichloromethane. The combined extract was dried over K2CO3 and evaporated to dryness. Fractional distillation gave the title product, b.p. 130-135° C./1.5 mm Hg. Yield 36.2 g (67%).

Workup

  1. temperatureThe resulting mixture was refluxed for 12 h
  2. extractionThe organic product was extracted with 4×300 ml of dichloromethane
  3. extractionThe combined extract
  4. dry with materialwas dried over K2CO3
  5. customevaporated to dryness
  6. distillationFractional distillation

Sources & evidence

ORD record
ord-18fcf72e1efa46c5b0d52b5cd35127ad
Source dataset
uspto-grants-2008_11
Patent number
US07446216B2

Linked notes

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