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

HRID 1469198ノート

反応式

HRID 1469198 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
50 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-555aa7f58a6e4defb8dc4616d2e8bb12
出典データセット
uspto-grants-2015_04
特許番号
US09006187B2

反応ノート

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