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

HRID 1271470노트

반응식

HRID 1271470 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

HCID 140034323-Bromo-7-phenyl-hexahydroazepin-2-one수율 76.9%

시약·촉매·용매 2

HCID 807Iodine촉매HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d831491effd2476da890585cd5680b36
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205292B2

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