Water → 2-((E)-2-(3-fluorophenyl)ethenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 34031

Reaction equation

HRID 34031 reaction equation
[CH3:1][C:2]1([CH3:9])[C:6]([CH3:8])([CH3:7])[O:5][BH:4][O:3]1.[F:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=[CH2:15].O>C1(C)C=CC=CC=1.C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Rh].[Rh]>[F:10][C:11]1[CH:12]=[C:13](/[CH:14]=[CH:15]/[B:4]2[O:5][C:6]([CH3:8])([CH3:7])[C:2]([CH3:9])([CH3:1])[O:3]2)[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 962WaterHCID 676913-FluorostyreneHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolane

Product 1

HCID 597970362-((E)-2-(3-fluorophenyl)ethenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Reagents, catalysts & solvents 2

HCID 6436379Rhodium, di-mu-chlorobis((1,2,5,6-eta)-1,5-cyclooctadiene)di-CatalystHCID 1140TolueneSolvent

Procedure

To a solution of 11 mg of chloro(1,5-cyclooctadiene)-rhodium(I) dimer and 0.61 mL of 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane in 15 mL toluene was added dropwise 1.0 mL of 3-fluorostyrene, and stirred at room temperature for 4 hours. The reaction solution was added with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resultant crude product was purified and separated by silica gel column chromatography (diethyl ether:n-hexane=1:19), to afford 311 mg of the title compound as a pale yellow oil.

Workup

  1. dry with materialdried over anhydrous magnesium sulfate
  2. customThe solvent was evaporated
  3. customthe resultant crude product was purified
  4. customseparated by silica gel column chromatography (diethyl ether:n-hexane=1:19)

Sources & evidence

ORD record
ord-19f3cf7530ff411ea7fc46d3b23c22cf
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Linked notes

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