Sodium Carbonate → Triisopropyl({3-methyl-5-[4-(trifluoromethoxy)phenyl]thien-2-yl}methoxy)silane

HRID 9674

Reaction equation

HRID 9674 reaction equation
[CH:1]([Si:4]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:5][CH2:6][C:7]1[S:8][C:9](B2OC(C)(C)C(C)(C)O2)=[CH:10][C:11]=1[CH3:12])([CH3:3])[CH3:2].Br[C:29]1[CH:34]=[CH:33][C:32]([O:35][C:36]([F:39])([F:38])[F:37])=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:1]([Si:4]([CH:22]([CH3:24])[CH3:23])([CH:25]([CH3:27])[CH3:26])[O:5][CH2:6][C:7]1[S:8][C:9]([C:29]2[CH:30]=[CH:31][C:32]([O:35][C:36]([F:37])([F:38])[F:39])=[CH:33][CH:34]=2)=[CH:10][C:11]=1[CH3:12])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 21986357Triisopropyl{[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thien-2-yl]methoxy}silane2×

Product 1

HCID 21986319Triisopropyl({3-methyl-5-[4-(trifluoromethoxy)phenyl]thien-2-yl}methoxy)silane

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of triisopropyl{[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thien-2-yl]methoxy}silane (intermediate 116, 0.40 g) in 1,2-dimethoxyethane (12 ml) and water (6 ml) was treated with 4-bromo-trifluoromethoxybenzene (0.26 g), sodium carbonate (0.26 g) and tetrakis(triphenylphosphine)palladium (0) (0.120 g). The reaction mixture was stirred at reflux for 2 hours and then partitioned between water and ethyl acetate. The aqueous layer was separated and extracted with further ethyl acetate and then the organic solutions combined and dried over magnesium sulfate. The crude product was purified by Si SPE using dichloromethane as eluent to give the title compound as a yellow gum.

Workup

  1. temperatureat reflux for 2 hours
  2. custompartitioned between water and ethyl acetate
  3. customThe aqueous layer was separated
  4. extractionextracted with further ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. customThe crude product was purified by Si SPE

Sources & evidence

ORD record
ord-e03a93a17363478b889d4c03be0565a7
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Linked notes

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