3-Bromotoluene → 2-(3-Methylphenyl)benzonitrile

HRID 976587

Reaction equation

HRID 976587 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[Li]C(C)(C)C.Br[C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[C:17]#[N:18]>[Cl-].[Cl-].[Zn+2].C1C=CC([P]([Ni]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:8][C:4]1[CH:3]=[C:2]([C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=2[C:17]#[N:18])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 115603-BromotolueneHCID 162722-BromobenzonitrileHCID 178418306HCID 178418306, compound

Product 1

HCID 13942432-(3-Methylphenyl)benzonitrileYield 46.7%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 178420538HCID 178420538, compoundCatalyst

Procedure

3-Bromotoluene (17.5 mmoles, 3.0 g) was reacted with t-BuLi (19.3 moles) and ZnCl2 (19.3 mmoles, 2.62 g) followed by a Ni(PPh3)4 coupling to 2-bromobenzonitrile (17.5 mmole, 3.2 g) as in Preparation 1. The intermediate was purified by chromatography over silica gel eluted with 20% ether in hexane to yield 1.58 g of 2-(3-methylphenyl)-benzonitrile (MS)

Workup

  1. customThe intermediate was purified by chromatography over silica gel
  2. washeluted with 20% ether in hexane

Sources & evidence

ORD record
ord-9ccc724f711f4fd3835b9e850991d580
Source dataset
uspto-grants-1997_03
Patent number
US05612360

Linked notes

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