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

HRID 2299260Notes

Reaction equation

HRID 2299260 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+].[Cl-].[NH4+]>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)ethanenitrileYield 67.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

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) is added to a solution of potassium t-butoxide (35 g; 0.31 mol) dissolved in DMSO (125 mL) dropwise slowly over a 1-hour period. After the addition, the mixture is further stirred for 4 hours at room temperature and then slowly poured into a stirred, ice-cold solution of ammonium chloride with vigorous stirring. The resulting tan precipitate is filtered, pressed, washed with methanol, and air-dried to give 20 g of the title compound as a pale yellow solid (67%): 1H nmr (400 MHz, CDCl3) d 2.30 (s, 6 H), 2.32 (s, 3 H), 5.76 (s, 1 H), 6.93 (s, 2 H), 7.12 (d, 1 H), 7.21 (dd, 1 H), 7.63 (t, 1 H), 8.63 (d, 1 H).

Workup

  1. additionAfter the addition
  2. filtrationThe resulting tan precipitate is filtered
  3. washwashed with methanol
  4. customair-dried

Sources & evidence

ORD record
ord-02eb91b0199a4c428052d3f42bc9e900
Source dataset
uspto-grants-2002_12
Patent number
US06495686B2

Reaction notes

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