Sodium Carbonate → HCID 87198202, compound

HRID 1690186Notes

Reaction equation

HRID 1690186 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22](I)=[C:21]([CH3:26])[CH:20]=2)=[C:14]([CH2:27][CH2:28][CH3:29])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].[CH:32](B1OC(C)(C)C(C)(C)O1)=[CH2:33].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O>[F:1][C:2]([F:31])([F:30])[C:3]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([CH:32]=[CH2:33])=[C:21]([CH3:26])[CH:20]=2)=[C:14]([CH2:27][CH2:28][CH3:29])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86639420HCID 86639420, compound

Product 1

HCID 87198202HCID 87198202, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-(1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl)-1-(4-iodo-3-methyl phenoxy)-2-propylbenzene (265 mg, 0.471 mmol) was dissolved in N,N-dimethylformamide (4.7 mL) and water (0.9 mL). The resultant mixture was sequentially added with vinylboronic acid pinacol ester (280 μL, 1.65 mmol), tetrakis triphenylphosphine palladium (54 mg, 0.0471 mmol), and sodium carbonate (300 mg, 2.83 mmol), and stirred at 80° C. for 1 hour. After completion of the reaction, the reaction solution was filtered using celite and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified using column chromatography (hexane/chloroform), and 4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-1-(3-methyl-4-vinylphenoxy)-2-propylbenzene (218 mg, yield >100%) was obtained as a yellow oil.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction solution was filtered
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified

Sources & evidence

ORD record
ord-a0fce742de2542b6b7a32af7e6f085a8
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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