Sodium Carbonate → HCID 1393595, 화합물

HRID 1879253노트

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HRID 1879253 반응식
[OH:1][CH2:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15](I)[CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Br:12][C:13]1[CH:14]=[C:15]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][OH:1])[CH:4]=2)[CH:16]=[CH:17][CH:18]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 2734662[3-(Hydroxymethyl)phenyl]boronic acid

생성물 1

HCID 1393595HCID 1393595, 화합물수율 80%

시약·촉매·용매 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a 0.2 M solution of [3-(hydroxymethyl)phenyl]boronic acid in DME were sequentially added 1-bromo-3-iodobenzene (0.83 eq.) and a 2M solution of Na2CO3 (3.0 eq.). The reaction mixture was degassed, trans-bis(triphenylphosphine)palladium(II) chloride (0.01 eq.) was added and it was stirred at 80° C. for 6 h. After cooling down to RT the reaction mixture was diluted with EtOAc and washed with saturated aq. NaHCO3, 1N HCl and brine. The residue was dried (Na2SO4) and evaporated under reduced pressure to afford an oil which was purified by flash chromatography (SiO2, PE:EtOAc=8:2) to afford the title compound 94 as an oil (80%). 1H NMR (400 MHz, DMSO-d6, 300 K) δ 7.87 (s, 1H), 7.71 (d, J 7.7, 1H), 7.66 (bs, 1H), 7.59 (t, J 6.8, 2H), 7.47 (t, J 7.7, 2H), 7.39 (d, J 7.7, 1H), 4.61 (s, 2H).

후처리

  1. customThe reaction mixture was degassed
  2. temperatureAfter cooling down to RT the reaction mixture
  3. washwashed with saturated aq. NaHCO3, 1N HCl and brine
  4. dry with materialThe residue was dried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customto afford an oil which
  7. customwas purified by flash chromatography (SiO2, PE:EtOAc=8:2)

출처 및 근거

ORD 기록
ord-24ffda31d254463b9b2c7c2a8f9e437f
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314062B2

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