Allyltributylstannane → Methyl 2-cyano-4-(prop-2-en-1-yl)benzoate

HRID 2173225Notes

Reaction equation

HRID 2173225 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:12]#[N:13])[CH:3]=1.[CH2:14]([Sn](CCCC)(CCCC)CCCC)[CH:15]=[CH2:16].[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>[C:12]([C:4]1[CH:3]=[C:2]([CH2:16][CH:15]=[CH2:14])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])#[N:13]

Participants

6

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 58484706Methyl 4-bromo-2-cyanobenzoate

Product 1

HCID 67515990Methyl 2-cyano-4-(prop-2-en-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of methyl 4-bromo-2-cyanobenzoate (230 mg, 0.96 mmol), allyl-tributyl-stannane (381 mg, 1.2 mmol), LiCl (126 mg, 2.87 mmol) and Pd(PPh3)4 (23 mg) in anhydrous toluene was refluxed under N2 overnight. Distilled off the solvent under reduce pressure, the residue was purified with prep-TLC to give the product methyl 2-cyano-4-(prop-2-en-1-yl)benzoate.

Workup

  1. temperaturewas refluxed under N2 overnight
  2. distillationDistilled off the solvent
  3. customthe residue was purified with prep-TLC

Sources & evidence

ORD record
ord-22b7bc4085c44f388eb315de9bbd67cd
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…