Sulfuric Acid → 4-Acetyl-2-bromobenzonitrile

HRID 1098761Notes

Reaction equation

HRID 1098761 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[Br:11].S(=O)(=O)(O)O.N([O-])=O.[Na+].[C:21]([Cu])#[N:22].[C-]#N.[K+]>C(O)(=O)C.O>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([C:21]#[N:22])=[C:3]([Br:11])[CH:4]=1)(=[O:10])[CH3:9]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 9032Potassium CyanideHCID 15152811-(4-Amino-3-bromo-phenyl)-ethanoneHCID 23668193Sodium NitriteHCID 178418546HCID 178418546, compound

Product 1

HCID 133472764-Acetyl-2-bromobenzonitrileYield 57.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

To a solution of the product obtained in step 1 (9.50 g, 44.38 mmol) in acetic acid (160 mL) was added sulfuric acid (95%, 7.4 mL) at 0° C. After stirring for 10 min a solution of NaNO2 (3.06 g, 44.38 mmol) in water (30 mL) was added slowly. Stirring was continued for 30 min. The reaction mixture was added drop wise to a solution of CuCN (3.975 g, 44.38 mmol) and KCN (8.667 g, 133.1 mmol) in water (60 mL). Stirring was continued for 30 min at 0° C. and 2 h at RT. Then the reaction mixture was poured into water (400 mL). Filtration of the resulting suspension gave the desired product as red solid (5.7 g, 57%), which was used in the following step without further purification.

Workup

  1. additionwas added slowly
  2. stirringStirring
  3. waitwas continued for 30 min at 0° C. and 2 h at RT
  4. filtrationFiltration of the resulting suspension

Sources & evidence

ORD record
ord-a70212f59c0740348a9204bfa1613e1f
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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