Sodium Hydroxide → 7-Fluoro-4-methylbenzofuran

HRID 1602392Notes

Reaction equation

HRID 1602392 reaction equation
CO[CH:3](OC)[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:7]=1[F:13].[OH-].[Na+]>C1(C)C=CC=CC=1>[F:13][C:7]1[C:6]2[O:5][CH:4]=[CH:3][C:11]=2[C:10]([CH3:12])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19611641HCID 19611641, compound

Product 1

HCID 196116757-Fluoro-4-methylbenzofuranYield 42.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 2-(2,2-dimethoxy-ethoxy)-1-fluoro-4-methyl-benzene (48 g) in toluene (50 ml) was added dropwise to a refluxing solution of polyphosphoric acid (100 g) in toluene (350 ml) under nitrogen. The mixture was heated under reflux for 3 h, cooled to room temperature and sodium hydroxide (2N; 800 ml) added. The mixture was extracted with ether (3×300 ml) and the combined organic extracts washed with brine (2×300 ml) and dried (MgSO4). The solvent was evaporated and the residue purified by column chromatography. Eluting with hexane gave the title compound as a pale yellow oil (14.2 g)

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 h
  3. extractionThe mixture was extracted with ether (3×300 ml)
  4. washthe combined organic extracts washed with brine (2×300 ml)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated
  7. customthe residue purified by column chromatography
  8. washEluting with hexane

Sources & evidence

ORD record
ord-4c4d490fa70f48d9bb014aacd81a4aa7
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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