Potassium Carbonate → HCID 86685048, compound

HRID 532158Notes

Reaction equation

HRID 532158 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].C([O-])([O-])=O.[K+].[K+].Br[C:26]([C:28]([F:31])([F:30])[F:29])=[CH2:27]>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>[Cl:9][C:6]1[CH:5]=[C:4]([C:26]([C:28]([F:31])([F:30])[F:29])=[CH2:27])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2726961-Propene, 2-bromo-3,3,3-trifluoro-HCID 532171642-(3,5-Dichloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 86685048HCID 86685048, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

The mixture of 2-(3,5-dichloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (160 mg, 0.56 mmol), K2CO3 (232 mg, 1.68 mmol), compound 2-bromo-3,3,3-trifluoroprop-1-ene (146 mg, 0.84 mmol) and Pd(PPh3)2Cl2 (39 mg, 0.1 mmol) in THF/H2O (2/1 mL) was stirred in a sealed tube at 80° C. for 3 h. It was partitioned between EA and H2O. The organic layer was washed with brine, dried over Na2SO4, concentrated under vacuum. The residue was purified by column chromatography to give the desired product (78 mg, 55% yield).

Workup

  1. customIt was partitioned between EA and H2O
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e9da581f626245b98e2aa19cfb9c5917
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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