Hydrochloric Acid → Methyl 2-(benzyloxy)-4-iodobenzoate

HRID 454457Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:15][C:16]1[CH:25]=[C:24]([I:26])[CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19].Cl>C(OCC)(=O)C.CN(C)C(=O)C>[CH2:7]([O:15][C:16]1[CH:25]=[C:24]([I:26])[CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Potassium carbonate (1.9 g) and benzyl bromide (1.2 mL) were sequentially added to an N,N-dimethylacetamide (20 mL) solution of methyl 2-hydroxy-4-iodobenzoate (2.5 g), followed by stirring at 80° C. for 1 hour. The reaction mixture was cooled to room temperature, and then 1 mol/L hydrochloric acid and ethyl acetate were added thereto. The organic layer was separated, washed with 1 mol/L hydrochloric acid and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 90-80% hexane/ethyl acetate] to obtain 3.3 g of methyl 2-(benzyloxy)-4-iodobenzoate as a yellow oily substance.

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe organic layer was separated
washwashed with 1 mol/L hydrochloric acid
dry with materiala saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 90-80% hexane/ethyl acetate]

Sources & evidence

ORD record: ord-eaf519960013447b88048e93c9cd3ecc
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492582B2

Reaction notes

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