1,2-Difluorobenzene → HCID 15093857, compound

HRID 345472Notes

Reaction equation

HRID 345472 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[F:8].[N:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1.[OH-].[Na+]>OS(O)(=O)=O>[F:1][C:2]1[CH:7]=[C:6]([CH:15]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([F:8])[CH:4]=2)[C:12]2[CH:13]=[CH:14][N:9]=[CH:10][CH:11]=2)[CH:5]=[CH:4][C:3]=1[F:8]

Participants

5

Reactant 3

HCID 97061,2-DifluorobenzeneHCID 133894-PyridinecarboxaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 15093857HCID 15093857, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mechanically stirred mixture of 49.0 g (0.43 mole) of 1,2-difluorobenzene, 20.6 g (0.19 mole) of pyridine-4-carboxaldehyde and 80 ml of concentrated H2SO4 was heated at 70° C. for 21 hours. The reaction mixture was poured over ice, and the icy mixture was made basic with 50% NaOH. The resulting mixture was extracted with CH2Cl2 and the CH2Cl2 solution was dried (MgSO4). The solvent was removed in vacuo to give 54.94 g (89.8%) of a solid. This was recrystallized from a mixture of CH2Cl2 and hexane to give 44.82 g (74.3%) of a crystalline solid, mp 79°-82° C. Proton NMR showed that this sample contained ~5% of the 2,3-difluoro isomer.

Workup

  1. additionThe reaction mixture was poured over ice
  2. extractionThe resulting mixture was extracted with CH2Cl2
  3. dry with materialthe CH2Cl2 solution was dried (MgSO4)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-21518d3a3d1e4d0bbb1a6c0732c885d6
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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