Dimethylformamide → 2-Fluoro-4,6-dihydroxybenzaldehyde

HRID 1004316Notes

Reaction equation

HRID 1004316 reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[OH:11][C:12]1[CH:13]=[C:14]([F:19])[CH:15]=[C:16]([OH:18])[CH:17]=1>O>[OH:11][C:12]1[CH:17]=[C:16]([OH:18])[CH:15]=[C:14]([F:19])[C:13]=1[CH:3]=[O:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 126587785-Fluororesorcinol

Product 1

HCID 220104032-Fluoro-4,6-dihydroxybenzaldehydeYield 27.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethylformamide (12.7 g) was added to vigorously stirred phosphorous oxychloride (14.4 g) at 0° C. The reaction mixture was stirred at this temperature for 30 minutes, then 3,5-dihydroxyfluorobenzene (6 g) was added. The sticky red syrup was allowed to warm to room temperature and stirred for 2 hours, then left to stand for 14 hours. Water (100 ml) was added and the mixture extracted three times with ethyl acetate (100 ml). The combined organic extracts were washed with brine (100 ml), dried over magnesium sulphate and evaporated. The residue was purified by flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:2, v/v). Fractions homogeneous in the required product were combined and evaporated to give an orange solid which was triturated with ethyl acetate to give the title compound (2 g) as a yellow solid.

Workup

  1. stirringstirred for 2 hours
  2. waitleft
  3. waitto stand for 14 hours
  4. extractionthe mixture extracted three times with ethyl acetate (100 ml)
  5. washThe combined organic extracts were washed with brine (100 ml)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residue was purified by flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:2
  9. customevaporated
  10. customto give an orange solid which
  11. customwas triturated with ethyl acetate

Sources & evidence

ORD record
ord-53da613a47ea48c2bfa223e4727ea800
Source dataset
uspto-grants-2000_04
Patent number
US06048893

Reaction notes

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