Hydrochloric Acid → 4-Bromo-2,6-difluorobenzaldehyde

HRID 1176939Notes

Reaction equation

HRID 1176939 reaction equation
C([N-]C(C)C)(C)C.[Li+].[Br:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=1.[CH:18](N1CCCCC1)=[O:19].Cl>O1CCCC1.O>[Br:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([CH:18]=[O:19])=[C:12]([F:17])[CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 174291-PiperidinecarboxaldehydeHCID 1363131-Bromo-3,5-difluorobenzeneHCID 2724682Lithium diisopropylamide

Product 1

HCID 27732904-Bromo-2,6-difluorobenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

55 ml (0.11 mmol) of 2 M lithium diisopropylamide are added with stirring at −70° C. to a solution of 19.3 g (0.1 mmol) of 1-bromo-3,5-difluorobenzene in 120 ml of dried tetrahydrofuran. After 30 minutes, N-formylpiperidine is added dropwise at this temperature. The mixture is allowed to warm to 0°. At about 0° C., the reaction mixture is poured into cold water, acidified using 10% HCl and extracted twice with methyl tert-butyl ether. The combined organic phases are washed with water, dried over Na2SO4 and filtered, and the solvent is removed under reduced pressure. The residue is filtered through SiO2 (heptane/dichloromethane 1:1), (yield: 17.6 g, 78%).

Workup

  1. temperatureto warm to 0°
  2. extractionextracted twice with methyl tert-butyl ether
  3. washThe combined organic phases are washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent is removed under reduced pressure
  7. filtrationThe residue is filtered through SiO2 (heptane/dichloromethane 1:1), (yield: 17.6 g, 78%)

Sources & evidence

ORD record
ord-1fb0e421b827440abfb537052fc52a8d
Source dataset
uspto-grants-2010_11
Patent number
US07842845B2

Reaction notes

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