Dimethylformamide → Ethyl 4-bromo-3-ethoxy-5-hydroxybenzoate

HRID 530974Notes

Reaction equation

HRID 530974 reaction equation
[H-].[Na+].CN(C=O)C.[Br:8][C:9]1[C:19]([OH:20])=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]=1[OH:21].I[CH2:23][CH3:24]>O>[Br:8][C:9]1[C:10]([OH:21])=[CH:11][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:18][C:19]=1[O:20][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 57419684Ethyl 4-bromo-3,5-dihydroxybenzoate

Product 1

HCID 90423209Ethyl 4-bromo-3-ethoxy-5-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% oil, 3.86 g) was added to a DMF (100 mL) solution of ethyl 4-bromo-3,5-dihydroxybenzoate (12.3 g), and the mixture was stirred at 00° C. for 30 minutes in a nitrogen atmosphere. Iodoethane (4.15 mL) was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (8.87 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe obtained organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2ea105de0e8449b4a6ae4d3fac184274
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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