2-Bromopyridine → 2-(2-Pyridinyl)-2-(2,4,6-trimethylphenyl)ethanenitrile

HRID 1792252Notes

Reaction equation

HRID 1792252 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH2:10][C:11]#[N:12].Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.CC(C)([O-])C.[K+].[NH4+].[Cl-]>CS(C)=O>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH:10]([C:3]1[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])[C:11]#[N:12]

Participants

6

Reactant 4

HCID 79732-BromopyridineHCID 25517Ammonium ChlorideHCID 5206982,4,6-TrimethylphenylacetonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 220341262-(2-Pyridinyl)-2-(2,4,6-trimethylphenyl)ethanenitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Add dropwise over a 1-hour period a mixed solution of 2-(2,4,6-trimethylphenyl)ethanenitrile (20 g; 0.126 mol) and 2-bromopyridine (35 g; 0.22 mol) in DMSO (25 mL) to a solution of potassium t-butoxide (35 g; 0.31 mol) dissolved in DMSO (125 mL). After the addition, stir the mixture for 4 h at ambient temperature and slowly pour into a stirred, ice-cold solution of NH4Cl with vigorous stirring. Filter the resulting tan precipitate, wash with MeOH, and air-dry to obtain the title compound as a pale yellow solid: 1H NMR (400 MHz, CDCl3) δ 2.30 (s, 6H), 2.32 (s, 3H), 5.76 (s, 1H), 6.93 (s, 2H), 7.12 (d, 1H), 7.21 (dd, 1H), 7.63 (t, 1H), 8.63 (d, 1H).

Workup

  1. additionAfter the addition
  2. filtrationFilter the resulting tan precipitate
  3. washwash with MeOH
  4. customair-dry

Sources & evidence

ORD record
ord-9fd399b1e47447c491fc9dd0e5816314
Source dataset
uspto-grants-2006_07
Patent number
US07074929B2

Reaction notes

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