2,6-Di-tert-butyl-4-methylphenol → 4-Ethenyl-2-fluoroaniline

HRID 238936Notes

Reaction equation

HRID 238936 reaction equation
[F:1][C:2]1[CH:8]=[C:7](I)[CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:10](C([Sn])=C(CCCC)CCCC)[CH2:11]CC.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>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>[F:1][C:2]1[CH:8]=[C:7]([CH:10]=[CH2:11])[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

6

Reactant 3

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 1856942-Fluoro-4-iodoanilineHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 220256474-Ethenyl-2-fluoroanilineYield 93%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-fluoro-4-iodoaniline (2.37 g, 10 mmol) in toluene (50 mL) was treated with tetrakis(triphenylphosphine)palladium (0.578 g, 0.5 mmol), tributylvinyltin (3.5 mL, 12 mmol) and a catalytic amount of 2,6-di-tert-butyl-4-methylphenol. After being heated at 100° C. for 1 h, the reaction mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:5) as eluant to afford 2-Fluoro-4-vinylaniline (20-1, LJO-324, 1.275 g, 93%) as a yellow oil.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-926e7f9b4a7b41be8c988492b8929abf
Source dataset
uspto-grants-2014_02
Patent number
US08642657B2

Reaction notes

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