Iodoethane → 2-Ethoxy-1-methoxy-4-nitro-benzene

HRID 1297102Notes

Reaction equation

HRID 1297102 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[OH:13])C.[H-].[Na+].[CH2:16](I)[CH3:17]>CN(C=O)C>[CH2:16]([O:13][C:5]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:4]=1[O:3][CH3:1])[CH3:17]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 684831692-Ethoxy-5-nitrophenol

Product 1

HCID 117901432-Ethoxy-1-methoxy-4-nitro-benzeneYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under an inert atmosphere at 0° C., add a solution of 10 g (59 mmol) of 2-ethoxy-5-nitrophenol dissolved in 125 ml of DMF, on a solution of 2.6 g (65 mmol) of 60% NaH in oil dissolved in 125 ml of DMF. After 30 minutes at room temperature, add dropwise 5.2 ml (65 mmol) of EtI at 0° C. Allow to stand at room temperature for 12 hours. Add 1.5 l of a water-ice mixture. Filter the precipitate and wash three times with 100 ml of water then once with 100 ml of pentane. One obtains 9.8 g of the abovenamed product in the form of a white powder. Yield: 93%. 1H-NMR (CDCl3, 300 MHz): d 1.52 (t, 3H, —CH3), 3.98 (s, 3H, OCH3), 4.20 (q, 2H, OCH2), 6.91 (d, 1H Ar), 7.75 (d, 1H Ar), 7.91 (dd,1H Ar).

Workup

  1. waitto stand at room temperature for 12 hours
  2. filtrationFilter the precipitate
  3. washwash three times with 100 ml of water

Sources & evidence

ORD record
ord-6e6f71fc97b243d8a3056fe94abbb0e9
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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