4-bromo-N,N-dimethylaniline → HCID 19431307, compound

HRID 1077405Notes

Reaction equation

HRID 1077405 reaction equation
[Mg].Br[C:3]1[CH:11]=[CH:10][C:6]([N:7]([CH3:9])[CH3:8])=[CH:5][CH:4]=1.[Si:12]([O:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][C:28]=1[O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C:25](=O)[CH2:24][CH2:23]2)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[Cl-].[NH4+]>C1COCC1>[Si:12]([O:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][C:28]=1[O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:31])[CH3:32])[CH2:25][CH:24]=[C:23]2[C:3]1[CH:11]=[CH:10][C:6]([N:7]([CH3:9])[CH3:8])=[CH:5][CH:4]=1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 114654-bromo-N,N-dimethylanilineHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 19431303HCID 19431303, compound

Product 1

HCID 19431307HCID 19431307, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
60 °C

Procedure

Magnesium (124 mg, 5.1 mmol) is covered with 1 ml of distilled THF and heated at 60° C. with stirring. A solution of 4-bromo-N,N-dimethylaniline (1.02 g, 5.1 mmol) in 5 ml of distilled THF is added dropwise over the course of 20 min. The reaction mixture is heated at reflux of the THF for 1 h. A solution of 5,6-di(tert-butyldimethylsilyloxy)indan-1-one (2 g, 5.1 mmol) in 10 ml of distilled THF is added dropwise at room temperature over the course of 5 min to this yellow-green solution. The mixture is brought to reflux for 20 h. The reaction mixture, which is violet in colour, is hydrolyzed by saturated aqueous ammonium chloride solution, then extracted with ethyl acetate. The organic phase is washed with saturated aqueous NaCl solution, then dried over MgSO4. The solvent is evaporated under reduced pressure. The desired product is purified by chromatography with an eluent: 9:1 hexane/ethyl acetate, and is obtained in the form of an oil (0.9 g; 36%)

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 20 h
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with saturated aqueous NaCl solution
  5. dry with materialdried over MgSO4
  6. customThe solvent is evaporated under reduced pressure
  7. customThe desired product is purified by chromatography with an eluent
  8. custom9:1 hexane/ethyl acetate, and is obtained in the form of an oil (0.9 g; 36%)

Sources & evidence

ORD record
ord-16d7511e36964d53a2fa087f584c47ec
Source dataset
uspto-grants-1996_08
Patent number
US05543298

Reaction notes

Loading…