Bromine → 6-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-one

HRID 1253635Notes

Reaction equation

HRID 1253635 reaction equation
[Br:1]Br.[Al+3].[Cl-].[Cl-].[Cl-].[CH3:7][C:8]1([CH3:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[CH2:9]1>>[Br:1][C:13]1[CH:12]=[C:11]2[C:16]([C:8]([CH3:18])([CH3:7])[CH2:9][C:10]2=[O:17])=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 24408BromineHCID 3046283,3-Dimethyl-1-indanoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 107763656-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-oneYield 27%

Procedure

Bromine (0.2 ml, 3.8 mmol, 1.2 eq.) was added to a mixture of AlCl3 (1.04 g, 7.8 mmol, 2.5 eq.) and 3,3-dimethyl-indan-1-one (500 mg, 3.1 mmol) at 100° C. and the reaction mixture was heated at same temperature for 40-45 min. TLC (10% ethyl acetate/hexanes) showed the major product formation with little starting material and dibromo product. The reaction mass was quenched with crushed ice and extracted with ethyl acetate (3×50 ml). The organic part was separated, dried over Na2SO4 and evaporated under reduced pressure. The crude compound was purified by column chromatography (silica gel, 10% ethyl acetate/hexanes) to give the desired compound as a pale yellow solid. Yield: 27% (280 mg, 0.85 mmol).

Workup

  1. temperaturethe reaction mixture was heated at same temperature for 40-45 min
  2. customThe reaction mass was quenched with crushed ice
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. customThe organic part was separated
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure
  7. customThe crude compound was purified by column chromatography (silica gel, 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6a09f53207cb4a83ae15ea53ad2d60b4
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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