Water → 1059185-97-5

HRID 1685378Notes

Reaction equation

HRID 1685378 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[C-:12]#[N:13].[Na+].[C:15](=[O:18])([O-])[O-].[NH4+:19].[NH4+].[OH2:21]>CCO>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([CH3:10])[NH:19][C:12](=[O:21])[NH:13][C:15]2=[O:18])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 517111Ammonium CarbonateHCID 5185963',5'-Difluoroacetophenone

Product 1

HCID 593704611059185-97-5

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 3′,5′-difluoroacetophenone (5.00 g, 32.0 mmol), sodium cyanide (4.71 g, 96.1 mmol), and ammonium carbonate (30.8 g, 320 mmol) was heated at 70° C. in EtOH (60 mL) and water (60 mL) for 4 h. The reaction mixture was cooled to ambient temperature and the resulting precipitate filtered and rinsed with water to produce a white solid. The filtrate was extracted with EtOAc (2×250 mL). The combined organic extracts were washed with brine (100 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was combined with the solid collected above to provide the title compound. MS: m/z=227 (M+1).

Workup

  1. filtrationthe resulting precipitate filtered
  2. washrinsed with water
  3. customto produce a white solid
  4. extractionThe filtrate was extracted with EtOAc (2×250 mL)
  5. washThe combined organic extracts were washed with brine (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customcollected above

Sources & evidence

ORD record
ord-7587add906ac411b87eb57b229e9654b
Source dataset
uspto-grants-2012_04
Patent number
US08148390B2

Reaction notes

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