Sodium Carbonate → {[(2,3-Dichloro-5-ethenylphenyl)methyl]oxy}(1,1-dimethylethyl)dimethylsilane

HRID 337585Notes

Reaction equation

HRID 337585 reaction equation
Br[C:2]1[CH:3]=[C:4]([Cl:18])[C:5]([Cl:17])=[C:6]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH:7]=1.[CH:19](B1OC(C)(C)C(C)(C)O1)=[CH2:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)CC.CN(C=O)C>[Cl:17][C:5]1[C:4]([Cl:18])=[CH:3][C:2]([CH:19]=[CH2:20])=[CH:7][C:6]=1[CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 66896768{[(5-Bromo-2,3-dichlorophenyl)methyl]oxy}(1,1-dimethylethyl)dimethylsilane

Product 1

HCID 66896286{[(2,3-Dichloro-5-ethenylphenyl)methyl]oxy}(1,1-dimethylethyl)dimethylsilane

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 10311-PropanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

{[(5-Bromo-2,3-dichlorophenyl)methyl]oxy}(1,1-dimethylethyl)dimethylsilane (1 eq.) from the previous step and 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1 eq.) were combined in a 2:1 (v/v) mixture of DMF:n-PrOH (0.11 M). To this solution was then added palladium(II) acetate (0.05 eq.) and triphenylphosphine (0.15 eq.) before the vessel was repeatedly evacuated and back-filled with nitrogen. Finally, 2 N aq. Na2CO3 (2 eq.) was added and the resulting biphasic suspension was heated at 90° C. for 8 h. The now black suspension was cooled to RT, diluted with water and extracted with 1:1 (v/v) hexanes:ether. The combined organic extracts were then washed further with 1 N aq. NaOH, water and brine. This was then dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford the crude title compound as a black oil.

Workup

  1. additionback-filled with nitrogen
  2. temperatureThe now black suspension was cooled to RT
  3. extractionextracted with 1:1 (v/v) hexanes
  4. washThe combined organic extracts were then washed further with 1 N aq. NaOH, water and brine
  5. dry with materialThis was then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-76c5fe832fa44caba0881fa4ba428475
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

Loading…