Bromine → HCID 66615593, compound

HRID 538857Notes

Reaction equation

HRID 538857 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH2:5]([CH:9]1[CH2:20][C:19]2[C:11](=[CH:12][C:13]3[CH2:14][CH2:15][CH2:16][C:17]=3[CH:18]=2)[C:10]1=[O:21])[CH:6]([CH3:8])[CH3:7].[Br:22]Br>ClCCl>[CH2:5]([CH:9]1[CH2:20][C:19]2[C:11](=[CH:12][C:13]3[CH2:14][CH2:15][CH2:16][C:17]=3[C:18]=2[Br:22])[C:10]1=[O:21])[CH:6]([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 24408BromineHCID 6451240Aluminum(III) ChlorideHCID 66615620HCID 66615620, compound

Product 1

HCID 66615593HCID 66615593, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 14.6 g (110 mmol) of AlCl3 in 40 ml of dichloromethane a solution of 10.0 g (43.8 mmol) of 2-isobutyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-one in 25 ml of dichloromethane was added dropwise by vigorous stirring at 0° C. Further on, 7.71 g (48.2 mmol) of bromine was added dropwise at this temperature. The resulting mixture was stirred overnight at room temperature and then poured on 500 cm3 of ice. The product was extracted by 3×200 ml of dichloromethane. The combined organic extract was washed by water, aqueous NaHCO3, dried over Na2SO4, and evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: hexanes-dichloromethane=3:1, vol.). Yield 9.40 g (70%) of the title product.

Workup

  1. additionwas added dropwise
  2. stirringThe resulting mixture was stirred overnight at room temperature
  3. extractionThe product was extracted by 3×200 ml of dichloromethane
  4. extractionThe combined organic extract
  5. washwas washed by water, aqueous NaHCO3
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: hexanes-dichloromethane=3:1, vol.)

Sources & evidence

ORD record
ord-bcbaeea4511b4da7a6688b0dade9a1af
Source dataset
uspto-grants-2014_10
Patent number
US08865848B2

Reaction notes

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