Potassium Carbonate → 1-Fluoro-2-(trifluoromethyl)-4-(3,3,3-trifluoroprop-1-en-2-yl)benzene

HRID 532189Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5](B2OCCO2)=[CH:4][C:3]=1[C:13]([F:16])([F:15])[F:14].Br[C:18]([C:20]([F:23])([F:22])[F:21])=[CH2:19].C([O-])([O-])=O.[K+].[K+]>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:18]([C:20]([F:23])([F:22])[F:21])=[CH2:19])=[CH:4][C:3]=1[C:13]([F:14])([F:15])[F:16]

Participants

Conditions

Temperature: 70 °C

Procedure

The mixture of 2-(4-fluoro-3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (2.34 g, 10 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (2.10 g, 12 mmol), Pd(Ph3P)2Cl2 (0.281 g, 0.4 mmol) and K2CO3 (2.76 g, 20 mmol) in THF (30 mL) and H2O (15 mL) was heated at 70° C. overnight. Then the reaction mixture was cooled down to rt, added water and extracted with ethyl acetate, washed with brine, dried with Na2SO4, concentrated to dryness to afford the crude product. It was further purified by column chromatography eluted with PE to afford the desired product (0.6 g, yield 23.3%) as light yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.69-7.62 (m, 2H), 7.27-7.21 (t, 1H), 6.05 (d, 1H), 5.80 (d, 1H) ppm.

Workup

temperatureThen the reaction mixture was cooled down to rt
extractionextracted with ethyl acetate
washwashed with brine
dry with materialdried with Na2SO4
concentrationconcentrated to dryness
customto afford the crude product
customIt was further purified by column chromatography
washeluted with PE

Sources & evidence

ORD record: ord-c5850f3b5ef641ba86656aee6d8103fc
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853186B2

Reaction notes

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