Potassium Phosphate, Tribasic → HCID 58319284, compound

HRID 2363107Notes

Reaction equation

HRID 2363107 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[CH:16]1(B(O)O)[CH2:18][CH2:17]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:9]([Si:6]([O:5][C:4]1[CH:13]=[CH:14][CH:15]=[C:2]([CH:16]2[CH2:18][CH2:17]2)[CH:3]=1)([CH3:8])[CH3:7])([CH3:12])([CH3:11])[CH3:10]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 11254705(3-Bromophenoxy)(tert-butyl)dimethylsilane

Product 1

HCID 58319284HCID 58319284, compoundYield 90.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 22272177Toluene waterSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of (3-bromo-phenoxy)-tert-butyl-dimethyl-silane (500 mg, 0.1.74 mmol), cyclopropyl boronic acid (194 mg, 2.26 mmol), K3PO4(1.3 g, 6.1 mmol), PCy3(49 mg, 0.17 mmol), and Pd(OAc)2 (20 mg, 0.087 mmol) in toluene/water (8 ml/0.4 ml) was stirred 3 hours at 110° C. and then diluted with Et2O. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography (gradient 12% to 100% EtOAc in n-hexane) to give tert-butyl-(3-cyclopropyl-phenoxy)-dimethyl-silane (390 mg, 90%).

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by column chromatography (gradient 12% to 100% EtOAc in n-hexane)

Sources & evidence

ORD record
ord-f42f84b0a9d34123a503b54270cbad59
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

Loading…