Hydrochloric Acid → 3-(3-Bromophenyl)-3-oxopropanenitrile

HRID 1400686Notes

Reaction equation

HRID 1400686 reaction equation
[C:1](#[N:3])[CH3:2].[H-].[Na+].[Br:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10](OC)=[O:11].Cl>C1COCC1.O>[Br:6][C:7]1[CH:8]=[C:9]([C:10](=[O:11])[CH2:2][C:1]#[N:3])[CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 12070Methyl 3-bromobenzoateHCID 24758Sodium hydride

Product 1

HCID 27568393-(3-Bromophenyl)-3-oxopropanenitrileYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

Acetonitrile (21.86 mL, 419 mmol) was added to a stirred suspension of 60% NaH (7.25 g, 181 mmol) in THF (150 mL). Then, methyl 3-bromobenzoate (30 g, 140 mmol) was added and the mixture was heated at 75° C. for 4 h. After cooling to room temperature, water followed by 1N HCl (200 mL) was added and the mixture was extracted with ethyl acetate (500 mL), washed with sat .NaHCO3 solution (200 mL), dried (Na2SO4), filtered and concentrated to afford 3-(3-bromophenyl)-3-oxopropanenitrile (29 g, 129 mmol, 93% yield) as light yellow solid. 1H NMR (500 MHz, CDCl3) δ 8.09 (t, J=1.7 Hz, 1H), 7.90-7.86 (m, 1H), 7.83 (ddd, J=8.0, 2.0, 1.1 Hz, 1H), 7.45 (t, J=7.9 Hz, 1H), 4.08 (s, 2H).

Workup

  1. temperatureAfter cooling to room temperature
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate (500 mL)
  4. washwashed
  5. dry with materialNaHCO3 solution (200 mL), dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c83f81f3cfba4044b76aa661febda7a2
Source dataset
uspto-grants-2014_12
Patent number
US08906929B2

Reaction notes

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