Acetonitrile → 2-(4-Iodophenyl)benzenecarbonitrile

HRID 1865062Notes

Reaction equation

HRID 1865062 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([NH2:12])=O)=[CH:4][CH:3]=1.C(#N)C.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]#[N:12])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 579748592-(4-Iodophenyl)benzamide

Product 1

HCID 13933592-(4-Iodophenyl)benzenecarbonitrileYield 95.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Add 2-(4-iodophenyl)benzamide (4.45 g, 0.0138 moles, preparation 56), acetonitrile (45 mL), and triethylamine (2.93 grams, 0.0289 moles) to a 100 mL 3-neck round-bottom flask equipped with a magnetic stirrer, internal temperature probe, ice-water bath, and addition funnel. Cool the contents of the 100 mL 3-neck round-bottom flask to 0° C. Add trifluoroacetic anhydride (3.04 grams, 0.0145 moles) to the reaction mixture via the addition funnel over 5 minutes. Observe a temperature increase to about 24° C., and cool the reaction mixture to 0° C. Stir the reaction mixture for 60 minutes. Add water (45 mL) and stir the suspension at ambient temperature for 60 minutes. Collect the precipitate by filtration and rinse the filter cake with water. Vacuum (15-25 mm) dry the filter cake at 50° C. to provide the title compound (4.03 g, 0.0132 moles) in 95.9% yield. 1H NMR(CDCl3, 500.0 MHz): δ 7.82 (app. d, 2H, J=9); 7.75 (dd, 1H, J=1.5, 8); 7.63 (dt, 1H, J=1.5, 7.5); 7.46 (d, 1H, J=8); 7.45 (dt, 1H, J=1.5, 7.5); 7.28 (app. d, 2H, J=8.5).

Workup

  1. customequipped with a magnetic stirrer
  2. temperatureObserve a temperature increase to about 24° C.
  3. temperaturecool the reaction mixture to 0° C
  4. customCollect the precipitate
  5. filtrationby filtration
  6. washrinse the filter cake with water
  7. customVacuum (15-25 mm) dry the filter cake at 50° C.

Sources & evidence

ORD record
ord-7cb3ed86102641878fdeb837087da598
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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