Iodoethane → 2-Bromo-1-ethoxy-4-nitrobenzene

HRID 1107294Notes

Reaction equation

HRID 1107294 reaction equation
I[CH2:2][CH3:3].[Br:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[OH:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:2]([O:14][C:6]1[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]=1[Br:4])[CH3:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 221092-Bromo-4-nitrophenol

Product 1

HCID 187870932-Bromo-1-ethoxy-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodoethane (3.7 ml) was added to a mixture of 2-bromo-4-nitrophenol (4 g) and potassium carbonate (5.1 g) in N,N dimethylformamide (20 ml) and the mixture was stirred at room temperature for 3 hours. The mixture was partitioned between water (300 ml) and ethyl acetate. After extraction with EtOAc. the combined organic fractions were washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/EtOAc (95:5 increasing to 90:10) to give the title compound as an oil (3.4 g). 1H NMR (250 MHz, CDCl3) δ 1.54 (3H, t, J=9.1 Hz), 4.21 (2H, q, J=7 Hz), 6.93 (1H, d, J=9.1 Hz), 8.19 (1H, dd, J=9.1, 2.7 Hz), and 8.47 (1H, d, J=2.7 Hz).

Workup

  1. customThe mixture was partitioned between water (300 ml) and ethyl acetate
  2. extractionAfter extraction with EtOAc
  3. washthe combined organic fractions were washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with hexane/EtOAc (95:5 increasing to 90:10)

Sources & evidence

ORD record
ord-913091976b7e46c8a5b17d01b9d5f7fb
Source dataset
uspto-grants-2000_05
Patent number
US06060469

Reaction notes

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