Potassium Cyanide → (2'-Chloro-3-methylbiphenyl-4-yl)acetonitrile

HRID 2194882Notes

Reaction equation

[C-:1]#[N:2].[K+].CS(O[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[CH:12][C:11]=1[CH3:23])(=O)=O>CN(C=O)C.O>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:13]1[CH:14]=[CH:15][C:10]([CH2:9][C:1]#[N:2])=[C:11]([CH3:23])[CH:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

KCN (1.1 eq.) was added to a stirred solution of (2′-chloro-3-methylbiphenyl-4-yl)methyl methanesulfonate (1 eq.) from step 2 in DMF (0.13M). The suspension was stirred 12 h. at 80° C. The final mixture was cooled down to room temperature, poured in water and extracted with Et2O. The organic extract was washed with water (2×), brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (0 to 50% in 30 min) to afforded the desired compound as a beige solid.

Workup

extractionextracted with Et2O
extractionThe organic extract
washwas washed with water (2×), brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel (Combi-Flash by ISCO)
washeluting with Hex/EtOAc (0 to 50% in 30 min)

Sources & evidence

ORD record: ord-a6932d4be06c40739e917da98be6f8bd
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334308B2

Reaction notes

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