Water → HCID 68710894, compound

HRID 2355005Notes

Reaction equation

HRID 2355005 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH:8]([CH3:10])[CH3:9].[CH3:11][O:12][C:13](=[O:22])[C:14]1[CH:19]=[C:18]([I:20])[CH:17]=[C:16]([OH:21])[CH:15]=1.O>CN(C)C=O.C(OC(=O)C)C>[CH3:11][O:12][C:13](=[O:22])[C:14]1[CH:19]=[C:18]([I:20])[CH:17]=[C:16]([O:21][CH:8]([CH3:10])[CH3:9])[CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 52987947Methyl 3-hydroxy-5-iodobenzoate

Product 1

HCID 68710894HCID 68710894, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

After adding 298 mg (2.16 mmol) of potassium carbonate and 0.12 ml (1.29 mmol) of 2-bromopropane to a solution of 120 mg (0.43 mol) of 3-hydroxy-5-iodobenzoic acid methyl ester in N,N-dimethylformamide (4.0 ml), the reaction mixture was stirred at 80° C. overnight. Water was added to the reaction mixture, extraction was performed with acetic acid ethyl ester, and then the organic layer was washed with brine, dried and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=5:1) to obtain 133 mg of 5-iodo-3-isopropoxybenzoic acid methyl ester (yield: 96%) as a colorless oil.

Workup

  1. washthe organic layer was washed with brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=5:1)

Sources & evidence

ORD record
ord-9875d447264f4fa79a51d2d4ac991ec5
Source dataset
uspto-grants-2010_07
Patent number
US07754743B2

Reaction notes

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