Potassium Carbonate → Methyl 5-(2-methoxyethoxy)-2-nitrobenzoate

HRID 631276

Reaction equation

HRID 631276 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][O:24][CH3:25]>CN(C=O)C.O>[CH3:25][O:24][CH2:23][CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 12922678Methyl 5-hydroxy-2-nitrobenzoate

Product 1

HCID 66639151Methyl 5-(2-methoxyethoxy)-2-nitrobenzoateYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To methyl 5-hydroxy-2-nitrobenzoate (1.08 g, 5.5 mmol) in DMF (50 mL) was added potassium carbonate (1.52 g, 11 mmol) followed by 1-bromo-2-methoxyethane (1.55 mL, 16.4 mmol) and the mixture heated at 60° C. overnight. After cooling to room temperature, the reaction was diluted with H2O, extracted with EtOAc, and the organic layer washed with H2O and brine, dried over MgSO4, filtered, concentrated in vacuo, and purified by column chromatography (12-100% EtOAc/hexanes) to give methyl 5-(2-methoxyethoxy)-2-nitrobenzoate (1.08 g, 4.2 mmol, 77%). 1H NMR (300 MHz, DMSO-d6) δ 8.13 (d, 1H), 7.31 (s, 1H), 7.29 (d, 1H), 4.29 (dd, 2H), 3.86 (s, 3H), 3.68 (dd, 2H), 3.31 (s, 3H); LC-MS (ESI) m/z 256 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc
  3. washthe organic layer washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (12-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4b9350ccd437411bad96225df5d6e392
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Linked notes

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