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

HRID 1271470Notes

Reaction equation

HRID 1271470 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-d831491effd2476da890585cd5680b36
Source dataset
uspto-grants-2007_04
Patent number
US07205292B2

Reaction notes

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