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

HRID 9674

반응식

HRID 9674 반응식
[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]

참가 물질

7

반응물 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}silane2회

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e03a93a17363478b889d4c03be0565a7
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091237B2

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