Sodium Cyanide → HCID 66678474, compound
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
Conditions
- Temperature
- 60 °C
Procedure
Methyl 2,4,5-trifluorobenzoate (DSL Chemicals; 950.61 mg; 5 mmol; 1 eq.), sodium cyanide (306.30 mg; 6.25 mmol; 1.25 eq.) and tetrabutylammonium bromide (2 014.82 mg; 6.25 mmol; 1.25 eq.) were dissolved in DMF (10 mL). The resulting mixture was heated at 60° C. overnight. As the reaction was not complete, sodium cyanide (306.30 mg; 6.25 mmol; 1.25 eq.) was added and the mixture was stirred at 60° C. for additional 24 h. The resulting dark pink solution was diluted with EtOAc and washed with brine several times. It was dried over MgSO4, filtrated and evaporated, resulting into a sticky dark red oil, which was purified by flash chromatography (SiO2 100 g, EtOAc/c-hex 1:9 until 1:1), affording the title product. 1H NMR (DMSO-d6, 300 MHz) δ 7.77 (dd, J=5.45, 8.41 Hz, 1H), 7.42 (dd, J=4.99, 8.88 Hz, 1H), 3.96 (s, 3H). LC/MS (Method A): 463.2 (M−H)−; 465.2 (M+H)+. HPLC (Method A) Rt 3.63 min (Purity: 99.9%).
Workup
- washwashed with brine several times
- dry with materialIt was dried over MgSO4
- filtrationfiltrated
- customevaporated
- customresulting into a sticky dark red oil, which
- customwas purified by flash chromatography (SiO2 100 g, EtOAc/c-hex 1:9 until 1:1)
Sources & evidence
- ORD record
- ord-5ced4d34ceda4ebf8e35c61db2934615
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202865B2
Reaction notes
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