Sodium Cyanide → 2-Fluoro-5-methylphenylacetonitrile

HRID 254502Notes

Reaction equation

HRID 254502 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[F:10].[C-:11]#[N:12].[Na+].C1OCCOCCOCCOCCOC1>C(#N)C>[F:10][C:4]1[CH:5]=[CH:6][C:7]([CH3:9])=[CH:8][C:3]=1[CH2:2][C:11]#[N:12]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 3633615-Crown-5HCID 177508002-(Bromomethyl)-1-fluoro-4-methylbenzene

Product 1

HCID 177506762-Fluoro-5-methylphenylacetonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(2-Fluoro-5-methyl-phenyl)-acetonitrile was prepared from 2-bromomethyl-1-fluoro-4-methyl-benzene and sodium cyanide in presence of a catalytic amount of 15-crown-5 in acetonitrile at ambient temperature over night in analogy to R. B. Katz et al., Tetrahedron 45, 1801 (1989): light yellow liquid; MS (EI): 149.1 (M+.).

Sources & evidence

ORD record
ord-8b2c5edc129c46168a3c157486cb367d
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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