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

HRID 2078255
Notes
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Reaction equation

HRID 2078255 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23676156Sodium t-butoxideHCID 513574012-(4-Chloro-2-iodophenyl)acetonitrile

Product 1

HCID 670999922-(4-Chloro-2-iodophenyl)propanenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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

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

Sources & evidence

ORD record
ord-a3d98c3ed2db4057ab8b35b9343f6709
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07928139B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes