Potassium Carbonate → HCID 86685048, compound

HRID 1750778Notes

Reaction equation

HRID 1750778 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-499f2019a1784650a56537e496518a8e
Source dataset
uspto-grants-2015_10
Patent number
US09156860B2

Reaction notes

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