1-(2,3-Dihydro-1H-inden-5-yl)ethan-1-one → 2-Bromo-1-(2,3-dihydro-1H-inden-5-yl)ethan-1-one

HRID 380567

Reaction equation

HRID 380567 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH2:8][CH2:7]2)(=[O:3])[CH3:2].[Br-:13].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.CO>[Br:13][CH2:2][C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH2:8][CH2:7]2)=[O:3]

Participants

4

Reactant 2

HCID 2339761-(2,3-Dihydro-1H-inden-5-yl)ethan-1-oneHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 131941252-Bromo-1-(2,3-dihydro-1H-inden-5-yl)ethan-1-oneYield 94.2%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 5-acetylindan (500 mg, 3.1 mmol) in dichloromethane-methanol (2:1, 15 ml) was added tetrabutylammonium tribromide (1.64 g, 3.4 mmol) was added at room temperature. After 23 h, the mixture was concentrated and the residue was partitioned between diethyl ether (50 ml) and water (50 ml). The organic layer was separated and washed with water (50 ml), brine (50 ml), and dried (MgSO4). Removal of solvent gave 698 mg (56%) of the title compound as white solids.

Workup

  1. additionwas added at room temperature
  2. concentrationthe mixture was concentrated
  3. customthe residue was partitioned between diethyl ether (50 ml) and water (50 ml)
  4. customThe organic layer was separated
  5. washwashed with water (50 ml), brine (50 ml)
  6. dry with materialdried (MgSO4)
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-b0b7b90b59604ae09134263686368630
Source dataset
uspto-grants-2001_10
Patent number
US06303628B1

Linked notes

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