Potassium Carbonate → HCID 69039983, compound

HRID 966087Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][O:6][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][C:10]([O:11][CH2:17][C:16]3[CH:19]=[CH:20][C:13]([F:12])=[CH:14][CH:15]=3)=[C:2]([F:1])[CH:3]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 3-fluoro-4-hydroxybenzoic acid (4.68 g, 30 mmol), 4-fluorobenzyl bromide (17.0 g, 90 mmol) and potassium carbonate (8.3 g, 60 mmol) in THF:water (1:1, 100 mL) was heated at 65° C. for 48 h. After cooling to room temperature the mixture was extracted with ethyl acetate (2×100 mL) and the combined extracts washed with brine (100 mL) and dried over sodium sulfate. Filtration and evaporation gave a residue which was crystallised from ether:heptane to afford the title compound (8.4 g, 75%) as a white solid. MS: m/e=372.0 (M+).

Workup

temperatureAfter cooling to room temperature the mixture
extractionwas extracted with ethyl acetate (2×100 mL)
washthe combined extracts washed with brine (100 mL)
dry with materialdried over sodium sulfate
filtrationFiltration and evaporation
customgave a residue which
customwas crystallised from ether

Sources & evidence

ORD record: ord-162b18df799d482ca02f4833a081d546
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951884B2

Reaction notes

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