Iodoethane → 2-Chloro-3-ethyl-4-fluorobenzonitrile

HRID 245049Notes

Reaction equation

HRID 245049 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].I[CH2:12][CH3:13]>>[Cl:1][C:2]1[C:9]([CH2:12][CH3:13])=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 6340IodoethaneHCID 1090002-Chloro-4-fluorobenzonitrile

Product 1

HCID 579086952-Chloro-3-ethyl-4-fluorobenzonitrileYield 28.2%

Procedure

The title compound is prepared by essentially following the procedure described in Preparation 1, using 2-chloro-4-fluoro-benzonitrile (12.2 g, 78.4 mmol), and iodoethane (18.4 g, 9.43 mL, 118 mmol). The crude product is purified on silica gel using 15-50% dichloromethane/hexanes to give the title compound as shiny white crystals (4.06 g, 28%). 1H-NMR (400 MHz, CDCl3) δ 7.54 (dd, J=5.6, 8.6 Hz, 1H), 7.07 (t, J=8.6 Hz, 1H), 2.85 (qd, J=7.5, 2.3 Hz, 2H), 1.19 (t, J=7.5 Hz, 3H).

Workup

  1. customThe title compound is prepared
  2. customdescribed in Preparation 1
  3. customThe crude product is purified on silica gel using 15-50% dichloromethane/hexanes

Sources & evidence

ORD record
ord-aa00fdd72b9e427f95409f35ca2235fd
Source dataset
uspto-grants-2014_02
Patent number
US08658693B2

Reaction notes

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