3,4-Dichlorobenzeneboronic acid → {[3-(3,4-Dichlorophenyl)-3-buten-1-yl]oxy}(1,1-dimethylethyl)diphenylsilane

HRID 639844Notes

Reaction equation

HRID 639844 reaction equation
Br[C:2](=[CH2:23])[CH2:3][CH2:4][O:5][Si:6]([C:19]([CH3:22])([CH3:21])[CH3:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][C:30]=1[Cl:31]>C1(C)C=CC=CC=1>[Cl:24][C:25]1[CH:26]=[C:27]([C:2](=[CH2:23])[CH2:3][CH2:4][O:5][Si:6]([C:19]([CH3:22])([CH3:21])[CH3:20])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:28]=[CH:29][C:30]=1[Cl:31]

Participants

4

Reactant 2

HCID 27343303,4-Dichlorobenzeneboronic acidHCID 11784074[(3-Bromo-3-buten-1-yl)oxy](1,1-dimethylethyl)diphenylsilane

Product 1

HCID 59255999{[3-(3,4-Dichlorophenyl)-3-buten-1-yl]oxy}(1,1-dimethylethyl)diphenylsilaneYield 64.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

[(3-Bromo-3-buten-1-yl)oxy](1,1-dimethylethyl)diphenylsilane (P12, 3.50 g) and (3,4-dichlorophenyl)boronic acid (2.06 g) were dissolved in toluene (45 mL), the stirred solution was degassed, then tetrakis(triphenylphosphine)palladium(0) (0.363 g) and ethanol (33 mL) were added and the mixture was degassed again. A 2N aqueous solution of Na2CO3 (24 mL) was added and the mixture was heated to 80° C. and stirred under nitrogen atmosphere for 3 h at this temperature. After cooling to RT, the reaction mixture was extracted with ethyl ether, the organic phase was washed with brine, dried over Na2SO4 and the solvent removed under reduced pressure. The crude product was purified by flash chromatography (eluting with cy/EA from 100/0 to 95/5) to give the title compound (2.65 g) as a colourless oil.

Workup

  1. customthe stirred solution was degassed
  2. additiontetrakis(triphenylphosphine)palladium(0) (0.363 g) and ethanol (33 mL) were added
  3. customthe mixture was degassed again
  4. additionA 2N aqueous solution of Na2CO3 (24 mL) was added
  5. temperatureAfter cooling to RT
  6. extractionthe reaction mixture was extracted with ethyl ether
  7. washthe organic phase was washed with brine
  8. dry with materialdried over Na2SO4
  9. customthe solvent removed under reduced pressure
  10. customThe crude product was purified by flash chromatography (eluting with cy/EA from 100/0 to 95/5)

Sources & evidence

ORD record
ord-81ad3a8982524a26a0d7e925f1374c4d
Source dataset
uspto-grants-2010_04
Patent number
US07691893B2

Reaction notes

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