Potassium Carbonate → HCID 68544214, 화합물

HRID 2242779

반응식

HRID 2242779 반응식
Br[C:2]1[S:6][C:5]([C:7]2[S:8][C:9](Br)=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.[Si:13]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][CH:28]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].[C:42](=[O:45])([O-])[O-].[K+].[K+]>C1COCC1.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>[Si:13]([O:45][CH2:42][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([C:2]2[S:6][C:5]([C:7]3[S:8][C:9]([C:30]4[CH:29]=[CH:28][C:27]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][O:20][Si:13]([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:14])[CH3:15])=[CH:32][CH:31]=4)=[CH:10][CH:11]=3)=[CH:4][CH:3]=2)=[CH:31][CH:32]=1)([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:15])[CH3:14]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 6389085,5'-Dibromo-2,2'-bithiopheneHCID 592073242-{4-[6-(Tert-butyl-dimethylsilanyloxy)hexyl]-phenyl}-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

생성물 1

HCID 68544214HCID 68544214, 화합물수율 64%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 5,5′-dibromo-[2,2′]bithiophene (0.60 g, 1.85 mmol) in anhydrous THF (50 ml) is added tetrakis(triphenylphosphine)palladium(0) (0.10 g) under N2, with stirring. After 20 min, 2-{4-[6-(tert-butyl-dimethylsilanyloxy)hexyl]-phenyl}-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (2.30 g, 5.50 mmol) and a solution of potassium carbonate (1.50 g) in water (10 ml) is added. This mixture is heated at reflux for 2 h. After cooling, water is added and the mixture is extracted with ethyl acetate (3×50 ml). The extracts are dried (Na2SO4) and evaporated under reduced pressure. The residue is purified by column chromatography on silica, eluting with petroleum ether/ethyl acetate (from 10:0 to 4:1), to give a yellow solid (0.87 g, 64%). 1H NMR (300 MHz, CDCl3): δ(ppm) 7.52 (d, J=8.1 Hz, 4H, Ar—H), 7.13-7.20 (m, 8H, Ar—H), 3.60 (t, J=6.4 Hz, 4H, OCH2), 2.62 (t, J=7.3 Hz, 4H, Ar—CH2), 1.35-1.65 (m, 16H, CH2), 0.89 (s, 18H, CH3), 0.05 (s, 12H, CH3); 13C NMR (75 MHz, CDCl3): δ(ppm) 143.2 (2×quat.), 142.5 (2×quat.), 136.3 (2×quat.), 131.5 (2×quat.), 129.0 (4×CH), 125.5 (4×CH), 124.3 (2×CH), 123.3 (2×CH), 63.3 (2×OCH2), 35.6 (2×CH2), 32.8 (2×CH2), 31.4 (2×CH2), 29.1 (2×CH2), 26.0 (3×CH3), 25.7 (CH2), 18.4 (2×quat.), −5.2 (2×CH3). HRMS 746.4080 (calc. for C44H66O2S2Si2 746.4043).

후처리

  1. temperatureThis mixture is heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling
  4. extractionthe mixture is extracted with ethyl acetate (3×50 ml)
  5. dry with materialThe extracts are dried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customThe residue is purified by column chromatography on silica
  8. washeluting with petroleum ether/ethyl acetate (from 10:0 to 4:1)

출처 및 근거

ORD 기록
ord-bab636f78a1c4ac498116adc818738c5
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674397B2

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