Sodium Cyanide → HCID 66678474, compound

HRID 2404322Notes

Reaction equation

HRID 2404322 reaction equation
[F:1][C:2]1[CH:11]=[C:10](F)[C:9]([F:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C-:14]#[N:15].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.CCOC(C)=O>[C:14]([C:10]1[C:9]([F:13])=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([F:1])[CH:11]=1)#[N:15]

Participants

6

Reactant 2

HCID 8929Sodium Cyanide2×HCID 14883312Methyl 2,4,5-trifluorobenzoate

Product 1

HCID 66678474HCID 66678474, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 2,4,5-trifluorobenzoate (DSL Chemicals, 950 mg, 5 mmol), sodium cyanide (306 mg, 6.25 mmol) and tetrabutylammonium bromide (2.01 g, 6.25 mmol) were dissolved in DMF (10 mL) and the resulting mixture was heated at 60° C. overnight. Additional amount of sodium cyanide (306 mg, 6.25 mmol) was added and the mixture was stirred at 60° C. for 24 additional hours. The reaction mixture was diluted with EtOAc and washed with brine several times. The organic layer was dried over MgSO4 and concentrated under vacuum. The residue was purified by flash chromatography (silica, EtOAc/cHex) to give the title compound. 1H NMR (DMSO-d6, 300 MHz) δ 7.77 (dd, J=8.4, 5.5 Hz, 1H), 7.42 (dd, J=8.9, 5.0 Hz, 1H), 3.96 (s, 3H). LC/MS (Method B): 463.2 (M−H)−, 465.2 (M+H)+. HPLC (Method A) Rt 3.63 min (Purity: 99.9%).

Workup

  1. washwashed with brine several times
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by flash chromatography (silica, EtOAc/cHex)

Sources & evidence

ORD record
ord-72e8b337f995464f89d745685f82c96a
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

Loading…