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

HRID 1873962Notes

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.C(OCC)(=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 Changzhou Fine Chemical Corp.) and potassium carbonate (3.6917 g; manufactured by Sigma-Aldrich Co.) were suspended in dehydrated DMF (21 mL; manufactured by Kanto Chemical Co., Inc.), added with benzyl bromide (1.22 mL; manufactured by Wako Pure Chemical Industries, Ltd.), and stirred at 50° C. overnight. After cooling to the room temperature, it was added to water and extraction was carried out twice with ethyl acetate. The organic layer was washed twice with water and once with brine and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=97:3→77:23) to obtain the title compound (2.2207 g).

Workup

temperatureAfter cooling to the room temperature, it
washThe organic layer was washed twice with water and once with brine
dry with materialdried over anhydrous sodium sulfate
customAfter 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-8c9bd8fdb2fd499eba19e79d0780b0a6
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304443B2

Reaction notes

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