Bromine → 3-Bromo-7-phenyl-hexahydroazepin-2-one

HRID 1271470ノート

反応式

HRID 1271470 の反応式
P(Cl)(Cl)(Cl)(Cl)Cl.[C:7]1([CH:13]2[NH:19][C:18](=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:21]Br>ClCCl.II>[Br:21][CH:17]1[CH2:16][CH2:15][CH2:14][CH:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:19][C:18]1=[O:20]

参加物

6

反応物 3

HCID 24408BromineHCID 24819Phosphorus pentachlorideHCID 105595527-Phenylazepan-2-one

生成物 1

HCID 140034323-Bromo-7-phenyl-hexahydroazepin-2-one収率 76.9%

試薬・触媒・溶媒 2

HCID 807Iodine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

Phosphorus pentachloride (4.95 g, 23.8 mmol) was added to a solution of 7-phenylazepan-2-one (4.50 g, 23.8 mmol) in dichloromethane (75 mL) at 0° C. After 1 h, iodine (0.060 g, 0.24 mmol) and a solution of bromine (1.22 mL, 23.8 mmol) in dichloromethane (10 mL) were added sequentially and the mixture was allowed to warm to ambient temperature. After 1.5 h, the reaction was quenched with aqueous sodium sulfite. The mixture was extracted with dichloromethane (3×), and the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography (10% ethyl acetate/hexanes→50% ethyl acetate/hexanes) gave the title compound (4.91 g). MS 268 (M+1).

後処理

  1. waitAfter 1.5 h
  2. customthe reaction was quenched with aqueous sodium sulfite
  3. extractionThe mixture was extracted with dichloromethane (3×)
  4. dry with materialthe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (10% ethyl acetate/hexanes→50% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-d831491effd2476da890585cd5680b36
出典データセット
uspto-grants-2007_04
特許番号
US07205292B2

反応ノート

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