Methyl iodide → 2-(4-Chloro-2-iodophenyl)propanenitrile

HRID 1868847Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[C:4]([I:11])[CH:3]=1.[CH3:12]C(C)([O-])C.[Na+].CI>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]#[N:10])=[C:4]([I:11])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(4-Chloro-2-iodophenyl)acetonitrile (1.070 g, 3.9 mmol) was dissolved in THF (50 mL) and cooled to 0° C. Sodium tert-butoxide (0.74 g, 7.7 mmol) was added, and the solution was stirred for 10 minutes (the reaction color changed from colorless to orange.) MeI (0.24 mL, 3.9 mmol) was then added dropwise as a solution in THF (10 mL). The reaction was complete in ten minutes as determined by TLC. The crude residue was purified by silica flash chromatography using 0-15% EtOAc/hexanes. MS m/e=292 (M+H)+.

Workup

waitThe reaction was complete in ten minutes
customThe crude residue was purified by silica flash chromatography

Sources & evidence

ORD record: ord-0b2f91b9490e4bfaa14229b14bba1c78
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635715B2

Reaction notes

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