Dimethylformamide → Methyl 4-iodo-2-isopropoxybenzoate

HRID 2272466Notes

Reaction equation

HRID 2272466 reaction equation
Br[CH:2]([CH3:4])[CH3:3].CN(C=O)C.[OH:10][C:11]1[CH:20]=[C:19]([I:21])[CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14].C(=O)([O-])[O-].[K+].[K+]>O>[I:21][C:19]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([O:10][CH:2]([CH3:4])[CH3:3])[CH:20]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 11380407Methyl 4-iodosalicylate

Product 1

HCID 90422834Methyl 4-iodo-2-isopropoxybenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Bromopropane (6.49 mL) was added to a DMF (70 mL) suspension of methyl 2-hydroxy-4-iodobenzoate (12.8 g) and potassium carbonate (12.7 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 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 (NH, hexane/ethyl acetate) to obtain the title compound (14.0 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 (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5a00b5eecc1447f0a1204df4631ed568
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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