Acetic Acid → 2-(4-Bromophenylamino)-2-(4-tert-butylphenyl)acetonitrile

HRID 1429261Notes

Reaction equation

HRID 1429261 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10].C(O)(=O)C.[C-:25]#[N:26].[K+]>C1COCC1.O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:17]([C:16]2[CH:19]=[CH:20][C:13]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:14][CH:15]=2)[C:25]#[N:26])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 78074-BromoanilineHCID 9032Potassium CyanideHCID 703244-tert-Butylbenzaldehyde

Product 1

HCID 582268062-(4-Bromophenylamino)-2-(4-tert-butylphenyl)acetonitrileYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromoaniline (10.0 g, 58.1 mmol) in THF (100 mL) was added 4-tert-butylbenzaldehyde (9.72 mL, 58.1 mmol), acetic acid (13.3 mL, 233 mmol), potassium cyanide (3.79 g, 58.1 mmol) and water (50 mL). The resultant mixture was stirred at room temperature for 16 hours. The resultant solid that formed was collected by vacuum filtration, washed with hexane, and then dried to afford 15.3 g, (77%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.49 (m, 4H), 7.37 (d, J=8.7 Hz, 2H), 6.66 (d, J=8.8 Hz, 2H), 5.34 (d, J=8.1 Hz, 1H), 4.02 (d, J=8.0 Hz, 1H), 1.34 (s, 9H).

Workup

  1. customThe resultant solid that formed
  2. filtrationwas collected by vacuum filtration
  3. washwashed with hexane
  4. customdried

Sources & evidence

ORD record
ord-48c10073326e4a34b044d9916885a981
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

Loading…