Allyltributylstannane → Methyl 5-nitro-2-(prop-2-en-1-yl)benzoate

HRID 1466096Notes

Reaction equation

HRID 1466096 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:15]([Sn](CCCC)(CCCC)CCCC)[CH:16]=[CH2:17].[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>[N+:12]([C:9]1[CH:10]=[CH:11][C:2]([CH2:17][CH:16]=[CH2:15])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5])([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 90628AllyltributylstannaneHCID 245494Methyl 2-Bromo-5-nitrobenzoateHCID 433294Lithium Chloride

Product 1

HCID 89524965Methyl 5-nitro-2-(prop-2-en-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of Methyl 2-bromo-5-nitrobenzoate (0.60 g, 2.3 mmol), allyl tri-n-butyltin (0.92 g, 2.8 mmol), lithium chloride (0.29 g, 6.9 mmol), and palladium tetrakis (0.13 g, 0.12 mmol) was heated to reflux for 16 hours in toluene. TLC showed formation of the desired product. The reaction was diluted with EtOAc, washed with brine, and separated. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography to obtain the title compound.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-9e22277aba6741988a0aa1d27376ebe6
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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