Hydrochloric Acid → 3-Ethyl-4-iodobenzonitrile

HRID 2189741Notes

Reaction equation

HRID 2189741 reaction equation
N[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][CH3:11].Cl.N([O-])=O.[Na+].[I-:17].[K+]>O>[CH2:10]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[I:17])[C:6]#[N:7])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 27353304-Amino-3-ethylbenzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 593167183-Ethyl-4-iodobenzonitrileYield 95.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To 4-amino-3-ethylbenzonitrile (2.50 g, 17.1 mmol) stirred in water (14 mL) at 0° C. was added concentrated hydrochloric acid (7.80 mL, 257 mmol) dropwise followed by a solution of sodium nitrite (1.24 g, 18.0 mmol) in water (3.43 mL) dropwise. The resultant mixture was stirred for 15 minutes and then added over 15 minutes to a solution of potassium iodide (2.98 g, 18.0 mmol) in water (6.0 mL) at 0° C. The mixture was stirred at room temperature for 2 h. The mixture was extracted with ethyl acetate (3×100 mL) and the combined organic fractions washed with brine (100 mL), dried (phase separator) and concentrated in vacuo to give the title compound as a brown solid (4.21 g, 16.4 mmol). δH (methanol-d4, 400 MHz): 8.02 (1H, d), 7.61 (1H, d), 7.24 (1H, dd), 2.80 (2H, q), 1.21 (3H, t).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
  2. washthe combined organic fractions washed with brine (100 mL)
  3. customdried (phase separator)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86a795a1885a4f94aef7806ffec77308
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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