Water → Methyl 4-(benzyloxy)-2-fluorobenzoate

HRID 1678717Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C=O)C>[CH2:19]([O:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([F:1])[CH:11]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl 2-fluoro-4-hydroxybenzoate (1.4685 g; manufactured by Changzou Fine Chemical Co., Ltd.) and potassium carbonate (3.6-917 g; manufactured by Sigma-Aldrich Co.) were suspended in dehydrated DMF (21 mL; manufactured by Kanto Chemical Co., Inc.), and benzyl bromide (1.22 mL; manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto. The mixture was stirred overnight at 50° C. The reaction solution was cooled to room temperature, and then was poured into water. The mixture was extracted two times with ethyl acetate. The organic layer was washed twice with water and once with brine, and was dried over anhydrous sodium sulfate. Subsequently, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=97:3→77:23). Thus, the title compound (2.2207 g) was obtained.

Workup

temperatureThe reaction solution was cooled to room temperature
extractionThe mixture was extracted two times with ethyl acetate
washThe organic layer was washed twice with water and once with brine
dry with materialwas dried over anhydrous sodium sulfate
customSubsequently, the solvent was evaporated under reduced pressure
customthe residue was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=97:3→77:23)

Sources & evidence

ORD record: ord-d391a0bf8ff244bc96a1e99d97c8de7e
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008506B2

Reaction notes

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