Iodine → 4-Fluoro-3-methylbenzaldehyde

HRID 1375002Notes

Reaction equation

HRID 1375002 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([CH3:8])[CH:7]=1.II.[Mg].[CH:13]([O-])([O-])[O:14]CC.S(=O)(=O)(O)O>C(OCC)C>[F:9][C:5]1[CH:4]=[CH:3][C:2]([CH:13]=[O:14])=[CH:7][C:6]=1[CH3:8]

Participants

7

Reactant 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 1235275-Bromo-2-fluorotolueneHCID 5462224MagnesiumHCID 53630039Ethylorthoformate

Product 1

HCID 27348744-Fluoro-3-methylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 5-bromo-2-fluorotoluene (6 g) in ethyl ether (10 ml) and a catalytic amount of iodine were added to a suspension of magnesium (960 mg) in ethyl ether (10 ml) under nitrogen atmosphere and the whole was refluxed for 30 minutes. After cooling, a solution of ethyl orthoformate (5.4 g) in ethyl ether (20 ml) was added to the mixture and the whole was stirred overnight. Sulfuric acid (10%, 20 ml) was added to the mixture and the organic layer was separated, washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel with a mixture of hexane and ethyl acetate (10:1) as eluent to give 4-fluoro-3-methylbenzaldehyde as an oil.

Workup

  1. temperaturethe whole was refluxed for 30 minutes
  2. temperatureAfter cooling
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel with a mixture of hexane and ethyl acetate (10:1) as eluent

Sources & evidence

ORD record
ord-98632e66786e46c59a1afab21c3c510e
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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