(4-Bromophenyl)boronic acid → HCID 68193265, compound

HRID 1626787Notes

Reaction equation

HRID 1626787 reaction equation
[C:1]([Si:5]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[Br:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>COCCOC>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([C:14]2[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][O:8][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6])=[CH:12][CH:13]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 79599(4-Bromophenyl)boronic acidHCID 58823820HCID 58823820, compound

Product 1

HCID 68193265HCID 68193265, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

tert-Butyl[2-(4-iodophenyl)ethoxy]dimethylsilane (7.1 g, 19.6 mmol), (4-bromophenyl)boronic acid (4.8 g, 23.9 mmol), tripotassium phosphate n-hydrate (10.4 g, 49.0 mmol) and a [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride dichloromethane complex (0.80 g, 0.98 mmol) were suspended in 1,2-dimethoxyethane (150 mL), followed by stirring at room temperature for 4 hours under a nitrogen atmosphere. After the reaction solution was filtered with celite, the filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane), and a fraction corresponding to the Rf value=0.90 (hexane/ethyl acetate=19/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (2.0 g, 5.1 mmol) as a white solid (yield 26%).

Workup

  1. filtrationAfter the reaction solution was filtered with celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane)
  4. concentrationa fraction corresponding to the Rf value=0.90 (hexane/ethyl acetate=19/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4f1f73238e9f45c4bdc84d7e4a805765
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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