Dimethylformamide → HCID 117992375, compound

HRID 531060Notes

Reaction equation

HRID 531060 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:12]=[C:13]([OH:16])[C:14]=1[I:15])[C:7]([O:9][CH2:10][CH3:11])=[O:8].CN(C=O)C.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[CH2:22]([O:3][C:4]1[CH:5]=[C:6]([CH:12]=[C:13]([OH:16])[C:14]=1[I:15])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 85971048HCID 85971048, compound

Product 1

HCID 117992375HCID 117992375, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% oil, 1.33 g) was added to a mixture of ethyl 3,5-dihydroxy-4-iodobenzoate (5.00 g) and DMF (50 mL), and the resultant mixture was stirred at 0° C. for 30 minutes in a nitrogen atmosphere. Benzyl bromide (2.78 g) 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 (2.94 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-8241c9c3ecbb4f8eb6dcf82d626f871c
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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