Potassium Phosphate, Tribasic → HCID 67111174, compound

HRID 2363134Notes

Reaction equation

HRID 2363134 reaction equation
[C:1]([Si:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[C:10]=1Cl)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[CH:20]1(B(O)O)[CH2:22][CH2:21]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1CCC(P(C2CCCCC2)C2CCCCC2)CC1>C1(C)C=CC=CC=1.O.CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([Si:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[C:10]=1[CH:20]1[CH2:22][CH2:21]1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 58319237HCID 58319237, compound

Product 1

HCID 67111174HCID 67111174, compound

Reagents, catalysts & solvents 3

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

Procedure

To a solution of tert-butyl-(2-chloro-3-trifluoromethyl-phenoxy)-dimethyl-silane (268 mg, 0.862 mmol), cyclopropyl boronic acid (96 mg, 1.12 mmol), K3PO4 (641 mg, 3.02 mmol), Pcy3 (24.2 mg, 0.086 mmol), and Pd(OAc)2 (9.7 mg, 0.043 mmol) in toluene/water (4 ml/0.2 ml) was stirred 3 hours at 110° C. and was diluted with Et2O. The residue was washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give the tert-butyl-(2-cyclopropyl-3-trifluoromethyl-phenoxy)-dimethyl-silane. To a suspension of tert-butyl-(2-cyclopropyl-3-trifluoromethyl-phenoxy)-dimethyl-silane in THF (5 mL) was added a solution of 1M-TBAF (1.12 mL, 1.3 eq), and then was stirred for 30 min at room temperature. The residue was diluted with EtOAc and water. The organic layer was washed with saturated ammonium chloride, water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography to give tert-butyl-(2-chloro-3-trifluoromethyl-phenoxy)-dimethyl-silane (53 mg, 30%).

Workup

  1. washThe residue was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5dc9d484760e4ceda2d65bc1d07a571a
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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