Water → 5-Fluoro-3-methylbenzofuran

HRID 226095

Reaction equation

[C:1]([C:4]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:5]=1[O:6][CH2:7]C(O)=O)(=O)[CH3:2].C([O-])(=O)C.[Na+].O>C(OC(=O)C)(=O)C>[F:15][C:13]1[CH:12]=[CH:11][C:5]2[O:6][CH:7]=[C:1]([CH3:2])[C:4]=2[CH:14]=1

Participants

Conditions

Temperature: 110 °C

Procedure

(2-Acetyl-4-fluoro-phenoxy)-acetic acid (1.87 gm, 8.8 mmol) is dissolved in acetic anhydride (60 mL) and treated with sodium acetate (10 gm, 0.12 mol). The resulting mixture is heated to 110° C. for 5 hr, then cooled to 0° C. H2O (100 mL) is added and the solution is stirred overnight at room temperature. The aqueous solution is then extracted into Et2O (2×75 mL). The combined organic extracts are washed with 3% aqueous KOH (2×75 mL), H2O (2×75 mL) and brine (1×75 mL), then dried over Na2SO4, filtered and concentrated. The crude product is purified by chromatography using hexane to give the title compound (1.07 gm, 81% yield).

Workup

temperaturecooled to 0° C
extractionThe aqueous solution is then extracted into Et2O (2×75 mL)
washThe combined organic extracts are washed with 3% aqueous KOH (2×75 mL), H2O (2×75 mL) and brine (1×75 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product is purified by chromatography

Sources & evidence

ORD record: ord-f885c5b69ce64084a3526fa07ea4d8af
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557103B2

Linked notes

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