Dimethylformamide → Ethyl 4-bromo-3-hydroxy-5-propoxybenzoate

HRID 531008Notes

Reaction equation

HRID 531008 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:14]([OH:15])=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]=1[OH:16].CN(C=O)C.I[CH2:23][CH2:24][CH3:25]>O>[Br:3][C:4]1[C:5]([O:16][CH2:23][CH2:24][CH3:25])=[CH:6][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][C:14]=1[OH:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 57419684Ethyl 4-bromo-3,5-dihydroxybenzoate

Product 1

HCID 90423420Ethyl 4-bromo-3-hydroxy-5-propoxybenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% oil, 10.1 g) was added to a mixture of ethyl 4-bromo-3,5-dihydroxybenzoate (30.0 g) and DMF (200 mL), and the resultant mixture was stirred at 0° C. for 30 minutes in a nitrogen atmosphere. 1-Iodopropane (11.2 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 (14.1 g).

Workup

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

Sources & evidence

ORD record
ord-4c3921d519e149b48e7c236842b61a0d
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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