Water → 5-Fluoro-3-methylbenzofuran

HRID 22736

Reaction equation

HRID 22736 reaction equation
C([O-])(=O)C.[Na+].[C:6]([C:9]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:10]=1[O:11][CH2:12]C(O)=O)(=O)[CH3:7].O>C(OC(=O)C)(=O)C>[F:20][C:18]1[CH:17]=[CH:16][C:10]2[O:11][CH:12]=[C:6]([CH3:7])[C:9]=2[CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 116585522-(2-Acetyl-4-fluorophenoxy)acetic acid

Product 1

HCID 116798475-Fluoro-3-methylbenzofuranYield 59%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
110 °C

Procedure

Anhydrous sodium acetate (139.3 mmol, 11.4 g) was added to a solution of the title compound of Example 14, Step A (3.24 mmol, 1.6 g) in acetic anhydride (70 mL) and heated for 3 hours at 110° C. After cooling, the reaction mixture was poured into water (100 mL) and stirred for 1 hour. The aqueous solution was extracted with ether (2×100 mL), washed with 3% aqueous KOH (2×20 mL) and water (2×20 mL). The washed ether layer was collected, dried, filtered and the filtrate was evaporated to a brown residue, which was purified by silica gel chromatography (eluent:hexanes) to obtain the desired product, 5-fluoro-3-methyl benzofuran (59%, 1.77 mg).

Workup

  1. temperatureAfter cooling
  2. extractionThe aqueous solution was extracted with ether (2×100 mL)
  3. washwashed with 3% aqueous KOH (2×20 mL) and water (2×20 mL)
  4. customThe washed ether layer was collected
  5. customdried
  6. filtrationfiltered
  7. customthe filtrate was evaporated to a brown residue, which
  8. customwas purified by silica gel chromatography (eluent:hexanes)

Sources & evidence

ORD record
ord-7bd01e2abf8d4b599991aaf826873f13
Source dataset
uspto-grants-2005_02
Patent number
US06849629B2

Linked notes

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