Sodium Carbonate → Benzaldehyde,2-benzo[b]thien-5-yl-

HRID 270012노트

반응식

HRID 270012 반응식
Br[C:2]1[CH:10]=[CH:9][C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=1.[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O)=[O:12].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[S:6]1[CH:7]=[CH:8][C:4]2[CH:3]=[C:2]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH:11]=[O:12])[CH:10]=[CH:9][C:5]1=2

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 2921892-Formylphenylboronic acidHCID 27765785-Bromo-1-benzothiophene

생성물 1

HCID 60139760Benzaldehyde,2-benzo[b]thien-5-yl-수율 81%

시약·촉매·용매 4

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

To a suspension of 5-Bromo-benzo[b]thiophene (compound PRE13) (3.68 g, 17.2 mmol) in toluene (183 mL) was added, under nitrogen, tetrakis(triphenylphosphine)-palladium (1.99 g, 1.72 mmol), then a solution of 2-formylphenylboronic acid (3.87 g, 25.8 mmol) in ethanol (20 mL) and at least dropwise aqueous sodium carbonate solution (3.64 g, 34.4 mmol) in water (20 mL). The reaction mixture was then heated to 80° C. for 3 h, cooled, concentrated, partitioned between ethyl acetate (120 mL) and water (70 mL) and acidified with hydrochloric acid (pH˜2). The organic layer was separated, dried over Na2SO4 and concentrated to give a crude residue that was purified by flash chromatography (silica, eluting solvent: (petroleum ether/AcOEt) 9.2/0.8) to give 3.31 g of compound PRE14 (orange yellow powder; yield=81%).

후처리

  1. additionwas added, under nitrogen
  2. temperaturecooled
  3. concentrationconcentrated
  4. custompartitioned between ethyl acetate (120 mL) and water (70 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give a crude residue that
  9. customwas purified by flash chromatography (silica, eluting solvent: (petroleum ether/AcOEt) 9.2/0.8)

출처 및 근거

ORD 기록
ord-7ee9c9f299ba4572b70062c261349b32
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449481B2

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