Dimethylformamide → HCID 90423102, compound

HRID 531014Notes

Reaction equation

HRID 531014 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.[CH2:14]([O:16][C:17]1[CH:18]=[C:19]([CH:25]=[C:26]([OH:29])[C:27]=1[I:28])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:1]([O:29][C:26]1[CH:25]=[C:19]([CH:18]=[C:17]([O:16][CH2:14][CH3:15])[C:27]=1[I:28])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 90422984HCID 90422984, compound

Product 1

HCID 90423102HCID 90423102, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Benzyl bromide (2.95 mL) was added to a DMF (200 mL) suspension of ethyl 3-ethoxy-5-hydroxy-4-iodobenzoate (7.59 g) and potassium carbonate (4.68 g), and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was allowed to cool to room temperature, and then, water was added thereto, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline and passed through a short silica gel (NH) column, and 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 (7.09 g).

Workup

  1. temperatureto cool to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe obtained organic layer was washed with saturated saline
  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-b2da0062f74546ffb670e462d031d7b7
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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