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

HRID 532189
Notes
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Reaction equation

HRID 532189 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2726961-Propene, 2-bromo-3,3,3-trifluoro-HCID 866850642-(4-Fluoro-3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

Product 1

HCID 866850651-Fluoro-2-(trifluoromethyl)-4-(3,3,3-trifluoroprop-1-en-2-yl)benzeneYield 23.3%

Reagents, catalysts & solvents 3

HCID 178418476
HCID 178418476, compound
Catalyst
HCID 962WaterSolvent2×
HCID 8028TetrahydrofuranSolvent

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

  1. temperatureThen the reaction mixture was cooled down to rt
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated to dryness
  6. customto afford the crude product
  7. customIt was further purified by column chromatography
  8. 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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