Ethyl bromoacetate → Ethyl(4-[2-methyl-2-nitropropyl]phenoxy)ethanoate

HRID 2119818Notes

Reaction equation

HRID 2119818 reaction equation
[CH3:1][C:2]([N+:12]([O-:14])=[O:13])([CH3:11])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH2:15]([O:17][C:18](=[O:21])[CH2:19]Br)[CH3:16].C(=O)([O-])[O-].[K+].[K+]>>[CH2:15]([O:17][C:18](=[O:21])[CH2:19][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][C:2]([CH3:1])([N+:12]([O-:14])=[O:13])[CH3:11])=[CH:5][CH:6]=1)[CH3:16]

Participants

4

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 128269024-(2-Methyl-2-nitropropyl)phenol

Product 1

HCID 22147737Ethyl(4-[2-methyl-2-nitropropyl]phenoxy)ethanoateYield 97.4%

Procedure

A mixture of 4-(2-methyl-2-nitropropyl)phenol (3.0 g, 15.4 mmol), ethylbromoacetate (2.04 mL, 17.0 mmol) and potassium carbonate (6.4 g, 46.2 mmol) was stirred at room temperature for 18 h. The reaction was concentrated in vacuo and the resulting residue partitioned between EtOAc and water. The layers were separated and the aqueous layer extracted with EtOAc (3×). The combined organic layers were washed with water (3×), brine, dried (Na2SO4), and concentrated in vacuo to a brown oil. The material was purified by flash chromatography over silica gel eluting with 5% MeOH/CHCl3 to provide 4.22 g (97%) of a clear oil. NMR

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe resulting residue partitioned between EtOAc and water
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with EtOAc (3×)
  5. washThe combined organic layers were washed with water (3×), brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo to a brown oil
  8. customThe material was purified by flash chromatography over silica gel eluting with 5% MeOH/CHCl3

Sources & evidence

ORD record
ord-8e1909bba90c4746901d9120ecfcf4c6
Source dataset
uspto-grants-2004_02
Patent number
US06686372B2

Reaction notes

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