1,2-Dimethoxyethane → 2-Cyano-4'-methylbiphenyl

HRID 1937099Notes

Reaction equation

HRID 1937099 reaction equation
[Li+].[Cl-].C(COC)OC.Br[C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]#[N:13].[C:18]1([CH3:26])[CH:23]=[CH:22][C:21]([Mg]Cl)=[CH:20][CH:19]=1>O1CCCC1>[C:18]1([CH3:26])[CH:23]=[CH:22][C:21]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[C:12]#[N:13])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 162722-BromobenzonitrileHCID 433294Lithium ChlorideHCID 178426149HCID 178426149, compound

Product 1

HCID 1455122-Cyano-4'-methylbiphenyl

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of MnCl2 (0.25 g, 1.98 mmol) and LiCl (0.17 g, 3.955 mmol) in a mixture of 2 ml of anhydrous tetrahydrofuran and 0.38 ml of dimethoxyethane (3.955 mol) is stirred at room temperature until, after approximately 30 minutes, a homogeneous medium is obtained. The PdCl2/dppp complex (0.0023 g, 0.1 mol %) and the o-bromobenzonitrile (0.72 g, 3 955 mmol) are then added and then a solution of p-tolylmagnesium chloride in tetrahydrofuran (1.80N, 2.86 ml, 5.14 mmol) is added over 30 minutes. After stirring for 30 minutes, the reaction mixture is treated as described in Example 4. The o-(p-tolyl)benzonitrile is thus obtained with a yield of isolated product of 95%.

Workup

  1. customa homogeneous medium is obtained
  2. stirringAfter stirring for 30 minutes
  3. additionthe reaction mixture is treated

Sources & evidence

ORD record
ord-950fedb948d44a0f950d84d03ef8fd62
Source dataset
uspto-grants-2002_05
Patent number
US06392080B1

Reaction notes

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