Methyl iodide → 4-Bromo-7-methoxy-6-nitro-2,3-dihydro-1H-inden-1-one

HRID 1661383Notes

Reaction equation

HRID 1661383 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([OH:14])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:15].N12CCCN=C1CCCC[CH2:17]2.IC.C(=O)([O-])O.[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([O:14][CH3:17])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:15]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 577812334-Bromo-7-hydroxy-6-nitro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 577812634-Bromo-7-methoxy-6-nitro-2,3-dihydro-1H-inden-1-oneYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-7-hydroxy-6-nitroindan-1-one (8.07 g, 29.7 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (5.33 mL, 35.6 mmol) were dissolved in N,N-dimethylformamide (150 mL), iodomethane (18.5 mL, 297 mmol) was added, and the mixture was stirred at room temperature for 40 hr. To the reaction solution was added saturated aqueous sodium hydrogencarbonate solution. The mixture was extracted with diethyl ether, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→60/40) to give the title compound (6.70 g, yield 79%).

Workup

  1. extractionThe mixture was extracted with diethyl ether
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→60/40)

Sources & evidence

ORD record
ord-31ed4cc479d94193867094facff38a87
Source dataset
uspto-grants-2011_10
Patent number
US08030337B2

Reaction notes

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