2-Nitrophenol → Methyl 5-bromo-2-(2-nitrophenoxy)valerate

HRID 414062Notes

Reaction equation

HRID 414062 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH:18]([CH2:23][CH2:24][CH2:25][Br:26])[C:19]([O:21][CH3:22])=[O:20]>CN(C)C=O>[Br:26][CH2:25][CH2:24][CH2:23][CH:18]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 10912698Methyl 2,5-dibromopentanoate

Product 1

HCID 21282573Methyl 5-bromo-2-(2-nitrophenoxy)valerate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-nitrophenol (0.7 g), powdery potassium carbonate (0.7 g), methyl 2,5-dibromovalerate (1.37 g) and dimethylformamide (10 ml) was stirred at room temperature for 4 hours, to which was added ice-water, followed by extraction with ether. The ether layer was washed with water and dried (MgSO4), then the solvent was distilled off. The residue was purified by means of silica gel chromatography [eluted with hexane-ethyl acetate (1:4)] to obtain methyl 5-bromo-2-(2-nitrophenoxy)valerate as an oily product. The yield was 1.30 g (77.8%).

Workup

  1. extractionfollowed by extraction with ether
  2. washThe ether layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by means of silica gel chromatography [eluted with hexane-ethyl acetate (1:4)]

Sources & evidence

ORD record
ord-5d618ad74303402c9e9de1d28ea5a5e4
Source dataset
uspto-grants-1988_12
Patent number
US04789675

Reaction notes

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