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

HRID 351351Notes

Reaction equation

HRID 351351 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

Conditions

Temperature
0 °C

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

Sources & evidence

ORD record
ord-211e7788f85e4019ba70b589bf761684
Source dataset
uspto-grants-2007_02
Patent number
US07183447B2

Reaction notes

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