Sodium Cyanide → (3',4'-Dichloro-2-fluoro-biphenyl-4-yl)-acetonitrile
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15]Br)=[CH:11][C:10]=2[F:17])[CH:5]=[CH:6][C:7]=1[Cl:8].[C-:18]#[N:19].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:18]#[N:19])=[CH:11][C:10]=2[F:17])[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
3′,4′-dichloro-2-fluoro-4-bromomethyl-biphenyl (35.0 g, 0.105 mol) and sodium cyanide (5.4 g, 0.110 mol) were dissolved in a mixture of ethanol (228 ml) and water (25 ml), then heated at 50° C. for 3 hours. The solution was concentrated under vacuum and the residue was suspended in ethanol/water 1/1 v/v (35 ml) and cooled at 0-5° C. for 30 minutes. The obtained solid is filtered and dried at 40° C. under vacuum. The crude product was suspended in ethanol (56 ml) at 20 to 25° C. for 30 minutes, filtered and dried at 40° C. under vacuum. The compound 3′,4′-dichloro-2-fluoro-4-cyanomethyl-biphenyl was obtained as a light brown powder (16.8 g, 57% yield).
Workup
- concentrationThe solution was concentrated under vacuum
- temperaturecooled at 0-5° C. for 30 minutes
- filtrationThe obtained solid is filtered
- customdried at 40° C. under vacuum
- filtrationfiltered
- customdried at 40° C. under vacuum
Sources & evidence
- ORD record
- ord-56cc1cdc437c4bfba16736f4e8bd4fd9
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08076505B2
Reaction notes
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