Ethanol → 4'-Methylsulfanyl-biphenyl-2-carbaldehyde

HRID 49180

반응식

HRID 49180 반응식
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:10][S:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.O>[CH3:10][S:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])=[CH:14][CH:13]=1

참가 물질

7

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 811292-BromobenzaldehydeHCID 27339594-(Methylthio)phenylboronic acid

생성물 1

HCID 13922174'-Methylsulfanyl-biphenyl-2-carbaldehyde수율 96.4%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

2-Bromobenzaldehyde (3.7 g, 20 mmol) and 4-(methylthio) benzeneboronic acid (3.36 g, 20 mmol) were dissolved in toluene (80 mL) and sodium carbonate (2M, 10 mL, 20 mmol) was added. To this reaction mixture was added ethanol (5 mL) followed by tetrakis (triphenylphosphine)palladium (240 mg, 0.2 mmol) and the reaction mixture was refluxed overnight under nitrogen atmosphere. The reaction mixture was cooled to room temperature and diluted with water (50 mL), stirred well, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water (2×50 mL), brine (1×50 mL), dried over sodium sulfate, filtered and the filtrate concentrated under reduced pressure to give the crude product. Purification by flash column chromatography using 5% ethyl acetate in hexane gave the title compound as a colorless thick oil (4.4 g, 96% yield). 1H NMR (CDCl3) δ9.98 (s, 1H), 8.01 (dd, J=7.8 Hz and 1.2 Hz, 1H), 7.6 (dt, J=7.5 and 1.4 Hz, 2H), 7.62-7.40 (m, 2H), 7.3-7.25 (m, 3H), 2.53 (s, 3H); LRMS (APIMS) m/z 329 (M+H)+.

후처리

  1. temperaturethe reaction mixture was refluxed overnight under nitrogen atmosphere
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with water (2×50 mL), brine (1×50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customto give the crude product
  9. customPurification by flash column chromatography

출처 및 근거

ORD 기록
ord-d0839809e87e4cd0b18befadcfa707df
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706724B2

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