4-Fluorobenzoyl chloride → (4-Fluorophenyl)-[2-methoxy-5-(5-methyl-7-nitroindan-4-yloxy)phenyl]methanone

HRID 1766667Notes

Reaction equation

HRID 1766667 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]2[C:16]([CH3:17])=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[C:13]3[C:9]=2[CH2:10][CH2:11][CH2:12]3)=[CH:5][CH:4]=1.[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([C:22]2[CH:21]=[C:6]([O:7][C:8]3[C:16]([CH3:17])=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[C:13]4[C:9]=3[CH2:10][CH2:11][CH2:12]4)[CH:5]=[CH:4][C:3]=2[O:2][CH3:1])=[O:29])=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 230311142,3-Dihydro-4-(4-methoxyphenoxy)-5-methyl-7-nitro-1H-indene

Product 1

HCID 23031124(4-Fluorophenyl)-[2-methoxy-5-(5-methyl-7-nitroindan-4-yloxy)phenyl]methanone

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

4-(4-methoxyphenoxy)-5-methyl-7-nitroindane (197 mg) and 4-fluorobenzoyl chloride (194 μL) were dissolved in dichloromethane (3.9 mL). Titanium tetrachloride (360 μL) was added dropwise to the solution under ice-cooling with stirring. The mixture was stirred under an argon atmosphere at room temperature for 15 hours. Adding water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=9/1) to give (4-fluorophenyl)-[2-methoxy-5-(5-methyl-7-nitroindan-4-yloxy)phenyl]methanone (155 mg).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred under an argon atmosphere at room temperature for 15 hours
  3. extractionAdding water, the reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, water and brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-a9715a64a6344683903b1f64aad39a1d
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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