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

HRID 1802682Notes

Reaction equation

HRID 1802682 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-9c2ea394dfb14b59a78f562d4f89e47c
Source dataset
uspto-grants-2013_01
Patent number
US08349879B2

Reaction notes

Loading…