Water → 5-Bromo-2,2-dimethylindan-1-one

HRID 1979075Notes

Reaction equation

HRID 1979075 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[CH3:12][C:13]([O-])([CH3:15])[CH3:14].[K+].[OH2:18]>C1COCC1>[CH3:12][C:13]1([CH3:15])[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2)[C:14]1=[O:18].[CH3:12][CH:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2)[C:7]1=[O:11]

Participants

6

Reactant 3

HCID 962WaterHCID 5206955-Bromo-1-indanone2×HCID 23665647Potassium tert-butoxide

Product 2

HCID 111391945-Bromo-2,2-dimethylindan-1-oneYield 43%HCID 148530085-Bromo-2-methyl-2,3-dihydro-1H-inden-1-oneYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-bromo-1-indanone (3.75 g, 17.76 mmol) in 18 ml of anhydrous THF is brought to −20° C. under an atmosphere of argon and with magnetic stirring. A 1M solution of t-BuOK in THF (18 ml, 18 mmol) is added with a syringe and the stirring continued for 3 hours at ambient temperature. At 0° C., 10 ml of distilled water is added and the mixture then extracted with ether (4×75 ml), dried over MgSO4, filtered and evaporated to obtain a raw product that is incorporated onto silica and purified by flash chromatography on silica (eluent ether:petroleum ether=2:98 up to 5:95). In order of elution, one obtains 1.85 g of a yellowish oil, 2,2-dimethyl-5-bromo-1-indanone (yield=43%), 0.50 g of a white solid 2-methyl-5-bromo-1-indanone (yield=13%) and 1.20 g of a white solid (32%) the starting material, 5-bromo-1-indanone.

Workup

  1. customis brought to −20° C. under an atmosphere of argon and with magnetic stirring
  2. extractionthe mixture then extracted with ether (4×75 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto obtain a raw product that
  7. custompurified by flash chromatography on silica (eluent ether:petroleum ether=2:98 up to 5:95)
  8. washIn order of elution, one

Sources & evidence

ORD record
ord-0c7f907df53e4290928789e2dfac314e
Source dataset
uspto-grants-2001_05
Patent number
US06239284B1

Reaction notes

Loading…