(o-Chlorophenyl)acetonitrile → 2-(2-Chlorophenyl)propanenitrile

HRID 1853906Notes

Reaction equation

HRID 1853906 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].[CH3:11][Si]([N-][Si](C)(C)C)(C)C.[Na+].CC1[IH]C=CC=1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:11])[C:9]#[N:10]

Participants

4

Reactant 3

HCID 76112(o-Chlorophenyl)acetonitrileHCID 2724254Sodium bis(trimethylsilyl)amideHCID 178418629HCID 178418629, compound

Product 1

HCID 126365722-(2-Chlorophenyl)propanenitrileYield 87%

Procedure

Following the procedure outlined for Example 649, 2-(2-chlorophenyl)acetonitrile (15 g, 98.9 mmol) was reacted with NaHMDS (118 mL, 118 mmol), and methyl iodie (7.0 mL, 108 mmol) to afford the desired product (14 g, 87%) as a brown oil: ESI MS m/z 166 [C9H8ClN+H]+.

Sources & evidence

ORD record
ord-190d27f4aa5f420db521776bd99fa6b6
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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