Sodium Chloride → 2-Bromo-3-phenyl-6-(3-phenylpropoxy)indane-1-one

HRID 17888

Reaction equation

HRID 17888 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:13][CH:14]=3)[C:9](=[O:26])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:27]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[Cl-].[Na+]>C(Cl)(Cl)(Cl)Cl.[W]>[Br:27][CH:8]1[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:13][CH:14]=2)[C:9]1=[O:26]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 686947433-Phenyl-6-(3-phenylpropoxy)indene-1-one

Product 1

HCID 686986112-Bromo-3-phenyl-6-(3-phenylpropoxy)indane-1-oneYield 60%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

3-Phenyl-6-(3-phenylpropoxy)indene-1-one (200 mg, 0.586 mmol) was dissolved in carbon tetrachloride, and N-bromosuccinimide (313 mg, 1.75 mmol) and 2,2′-azobisisobutyronitrile (9.7 mg) were added thereto. Then, the mixture was refluxed for 1 hour under a 375 W tungsten lamp. After the reaction was completed, saturated sodium chloride was added thereto and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography (ethyl acetate:hexane=1:5) to obtain title compound (147 mg, yield 60%) as a red solid.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customthe resulting residue was purified by column chromatography (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-ed396cf9a44d4f77bc2069f108568801
Source dataset
uspto-grants-2010_06
Patent number
US07741323B2

Linked notes

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