Hydrochloric Acid → 2,6-Difluoro-4-(5-pentylpyrimidin-2-yl)benzonitrile
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[N:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][N:11]=2)[CH:5]=[C:6]([F:9])[C:7]=1Br.[Cu][C:22]#[N:23].CN1CCCC1=O.Cl>[Fe](Cl)(Cl)Cl.O>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[N:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][N:11]=2)[CH:5]=[C:6]([F:9])[C:7]=1[C:22]#[N:23]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
0.7 g of 2-(3',5'-difluoro-4'-bromophenyl)-5-pentylpyrimidine, 0.5 g of copper (I) cyanide and 3.5 ml of N-methylpyrrolidone were mixed in a flask and refluxed for 5 hours. The solution was poured into a solution including 1.7 g of iron (III) chloride, 0.4 ml of concentrated hydrochloric acid and 1.7 ml of water. The solution was extracted with chloroform and washed with water and an aqueous 10% solution of potassium hydroxide. The chloroform was distilled off. The residue was treated through a silica gel column using chloroform as the solvent and recrystallized from methanol to yield 0.25 g of 2-(3',5'-difluoro-4'-cyanophenyl)-5-pentylpyrimidine. The crystal--isotropic liquid transfer point (C-I Point) of the compound was 65.3° C.
Workup
- temperaturerefluxed for 5 hours
- additionThe solution was poured into a solution
- extractionThe solution was extracted with chloroform
- washwashed with water
- distillationThe chloroform was distilled off
- additionThe residue was treated through a silica gel column
- customrecrystallized from methanol
Sources & evidence
- ORD record
- ord-23a5f7ea8963411583131eae81098fad
- Source dataset
- uspto-grants-1991_07
- Patent number
- US05030382
Reaction notes
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