Allyltributylstannane → HCID 69087457, compound

HRID 1466030Notes

Reaction equation

HRID 1466030 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1.[CH2:11]([Sn](CCCC)(CCCC)CCCC)[CH:12]=[CH2:13].[Cl-].[Li+]>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>[CH2:13]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1)[CH:12]=[CH2:11]

Participants

6

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 70104204-Bromo-2-chlorobenzonitrile

Product 1

HCID 69087457HCID 69087457, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-bromo-2-chlorobenzonitrile (22 mg, 1.0 mmol), allyl tri-n-butylstannane (400 mg, 1.2 mmol), lithium chloride (126 mg, 3.0 mmol), and Pd(PPh3)4, (18 mg, 0.04 mmol) in toluene (10 mL), was refluxed overnight. Then the reaction was quenched with aq. KF (10 mL), extracted with ethyl acetate (10 mL×3), dried over Na2SO4, concentrated in vacuo. The residue was purified by chromatography to give the title product.

Workup

  1. temperaturewas refluxed overnight
  2. customThen the reaction was quenched with aq. KF (10 mL)
  3. extractionextracted with ethyl acetate (10 mL×3)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-4890e20d480a4e38ad7b4ec2baab574d
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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