Water → (5-Bromo-3-methylthiophen-2-yl)(4-propylphenyl)methanone

HRID 1469198노트

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HRID 1469198 반응식
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=1)=[O:8].[Br-:18].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>C(O)(=O)C>[Br:18][C:5]1[S:4][C:3]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)=[O:8])=[C:2]([CH3:1])[CH:6]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 21124087PyridiniumtribromideHCID 43462760(3-Methylthiophen-2-yl)(4-propylphenyl)methanone

생성물 1

HCID 66691033(5-Bromo-3-methylthiophen-2-yl)(4-propylphenyl)methanone수율 64.4%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
50 °C

실험 절차

To a solution of (3-methylthiophen-2-yl)(4-propylphenyl)methanone (44, 1.12 g, 4.58 mmol) in acetic acid (4.67 mL) was added pyridinium tribromide (3.67 g, 11.5 mmol). The reaction mixture was heated to 50° C. for 3 hours. After cooling to room temperature, the mixture was poured into water (50 mL) and extracted with EtOAc (100 mL). The organic phase was dried over MgSO4 and evaporated under vacuum. The residue was further purified by silica column chromatography (Biotage) to provide (5-bromo-3-methylthiophen-2-yl)(4-propylphenyl)methanone (45, 0.95 g, 2.95 mmol, 64%).

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc (100 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated under vacuum
  5. customThe residue was further purified by silica column chromatography (Biotage)

출처 및 근거

ORD 기록
ord-555aa7f58a6e4defb8dc4616d2e8bb12
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006187B2

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