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

HRID 1937098Notes

Reaction equation

HRID 1937098 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.Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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

7

Reactant 4

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

Product 1

HCID 1455122-Cyano-4'-methylbiphenyl

Reagents, catalysts & solvents 2

HCID 11017392(1,3-Bis(diphenylphosphino)propane)palladium(II) chlorideCatalystHCID 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 mmol) is stirred at room temperature. After stirring for approximately 30 minutes, a homogeneous medium is obtained. The addition is then so carried out of 1/1: PdCl2/dppp (0.023 g, 1 mol %) and of o-bromobenzonitrile (0.72 g, 3.955 mmol) and then a solution of p-tolylmagnesium chloride in tetrahydrofuran (1.80N, 2.86 ml, 5.14 mmol) is added over 2 hours at room temperature. After stirring for 90 minutes, the reaction mixture is treated as described in Example 1. The o-(p-tolyl)benzonitrile is thus obtained with a yield of isolated product of 95%.

Workup

  1. stirringAfter stirring for approximately 30 minutes
  2. customa homogeneous medium is obtained
  3. additionThe addition
  4. stirringAfter stirring for 90 minutes
  5. additionthe reaction mixture is treated

Sources & evidence

ORD record
ord-5acca62d383e459c9c27e18d69ca5c74
Source dataset
uspto-grants-2002_05
Patent number
US06392080B1

Reaction notes

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