Allyltributylstannane → HCID 9816037, compound

HRID 1466118Notes

Reaction equation

HRID 1466118 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[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])=[CH:3][C:4]=1[C:11]([F:14])([F:13])[F:12])([O-:10])=[O:9]

Participants

7

Reactant 3

HCID 90628AllyltributylstannaneHCID 1361715-Bromo-2-nitrobenzotrifluorideHCID 433294Lithium Chloride

Product 1

HCID 9816037HCID 9816037, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-bromo-1-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-3a50eace52d24b02babf454b7a323e00
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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