Allyltributylstannane → Benzene, 4-nitro-1-(2-propen-1-yl)-2-(trifluoromethyl)-

HRID 1466120Notes

Reaction equation

HRID 1466120 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH2:15]([Sn](CCCC)(CCCC)CCCC)[CH:16]=[CH2:17].[Cl-].[Li+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.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+:8]([C:5]1[CH:6]=[CH:7][C:2]([CH2:17][CH:16]=[CH2:15])=[C:3]([C:11]([F:14])([F:13])[F:12])[CH:4]=1)([O-:10])=[O:9]

Participants

7

Reactant 3

HCID 90628AllyltributylstannaneHCID 1361982-Bromo-5-nitrobenzotrifluorideHCID 433294Lithium Chloride

Product 1

HCID 9816036Benzene, 4-nitro-1-(2-propen-1-yl)-2-(trifluoromethyl)-

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-bromo-4-nitro-2-(trifluoromethyl)benzene (1.0 g, 3.7 mmol), Allyl Tri-n-butyltin (1.4 mL, 4.4 mmol), Lithium Chloride (470 mg, 11 mmol), and Palladium Tetrakis (210 mg, 0.18 mmol) in toluene (30 mL) was heated to reflux for 16 hours under nitrogen. TLC showed complete reaction at that point. The reaction was diluted with ethyl acetate, adsorbed onto silica gel, and purified by silica gel chromatography to afford the title product.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours under nitrogen
  3. customreaction at that point
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-7f88ea31ffa94c30b451d58c8701fb8c
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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