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

HRID 49180

反応式

HRID 49180 の反応式
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

参加物

7

反応物 4

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

生成物 1

HCID 13922174'-Methylsulfanyl-biphenyl-2-carbaldehyde収率 96.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-d0839809e87e4cd0b18befadcfa707df
出典データセット
uspto-grants-2004_03
特許番号
US06706724B2

関連ノート

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