Water → 3-Trifluoromethyl-4-vinylaniline

HRID 2070033Notes

Reaction equation

Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].O.[C:14](N)(C)(C)[CH3:15].FC(OB([O-])[O-])=C(F)F.[K+].[K+]>C(O)(C)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:10][C:9]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:2]=1[CH:14]=[CH2:15])[NH2:6]

Participants

Conditions

Temperature: 80 °C

Procedure

4-Bromo-3-(trifluoromethyl)aniline (4.0 g, 16.7 mmol) was dissolved in isopropanol (20 mL), water (10 mL), and t-butylamine (5 mL). To the solution, potassium(trifluoro)vinylborate (4.0 g, 29.9 mmol), PdCl2(dppf)2.2-dichloromethane complex (300 mg, 0.37 mmol) were added. The resulting mixture was stirred under argon atmosphere at 80° C. for 20 hours and then concentrated. The residue was partitioned between water and ethyl acetate, and the organic layer was washed with saturated brine and concentrated under reduced pressure. The resulting product was purified by silica-gel column chromatography (n-hexane:ethyl acetate=6:1) to give 3-trifluoromethyl-4-vinylaniline (2.475 g, 79%) as a light-yellow oil.

Workup

addition2-dichloromethane complex (300 mg, 0.37 mmol) were added
concentrationconcentrated
customThe residue was partitioned between water and ethyl acetate
washthe organic layer was washed with saturated brine
concentrationconcentrated under reduced pressure
customThe resulting product was purified by silica-gel column chromatography (n-hexane:ethyl acetate=6:1)

Sources & evidence

ORD record: ord-6eb1ebd3178146babfd787f8b81ef64f
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299252B2

Reaction notes

Loading…