Tributylvinyltin → 3-Ethenyl-6-fluoro-2-methylbenzonitrile

HRID 1474257Notes

Reaction equation

HRID 1474257 reaction equation
Br[C:2]1[C:3]([CH3:11])=[C:4]([C:7]([F:10])=[CH:8][CH:9]=1)[C:5]#[N:6].[CH2:12]([Sn](CCCC)(CCCC)C=C)[CH2:13]CC.[Li+].[Cl-]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([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>[CH:12]([C:2]1[C:3]([CH3:11])=[C:4]([C:7]([F:10])=[CH:8][CH:9]=1)[C:5]#[N:6])=[CH2:13]

Participants

6

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 666438523-Bromo-6-fluoro-2-methylbenzonitrile

Product 1

HCID 666438663-Ethenyl-6-fluoro-2-methylbenzonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 3-bromo-6-fluoro-2-methylbenzonitrile (8.8 g, 41 mmol), tributyl(vinyl)tin (14.3 g, 45.2 mmol), LiCl (5.20 g, 123 mmol) and Pd(PPh3)4 (2.3 g, 2.0 mmol) in toluene (200 mL) was heated at 100-110° C. under N2 overnight. The mixture was concentrated and the residue was purified by column chromatography to obtain 3-ethenyl-6-fluoro-2-methylbenzonitrile.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-bd49f2007c0447449f5b21fd36c523a7
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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