Bromine → HCID 22105480, compound

HRID 1456635Notes

Reaction equation

HRID 1456635 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][CH:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:6]=2[CH:20]=1.[Br:21]Br>C(Cl)(Cl)(Cl)Cl>[Br:21][CH:9]1[CH:8]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[C:6]2[CH:20]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[NH:11][C:10]1=[O:12]

Participants

4

Reactant 2

HCID 24408BromineHCID 22105454HCID 22105454, compound

Product 1

HCID 22105480HCID 22105480, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1-benzazepin-2-one (0.378 g, 1.31 mmole) in 45 mL of dry carbon tetrachloride was heated to reflux, which generated a clear solution. Bromine (0.15 mL, 2.91 mmole) was added in two portions, 20 minutes apart, and the solution was heated at reflux for a total of 1 hour under a sunlamp. After cooling the reaction solution was washed sequentially with 5% aqueous sodium thiosulfate, dilute aqueous sodium bicarbonate, and 5% aqueous sodium thiosulfate. The organic phase was dried (sodium sulfate) and concentrated. The crude material was purified using a 2 mm chromatotron plate, eluting with 1:1 ethyl acetate-hexane, yielding 0.185 g (72%) of the title compund. IR(KBr): 3386, 1731, 1682 cm-1. Mass spec. (EI, m/z 367).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperaturethe solution was heated
  4. temperatureat reflux for a total of 1 hour under a sunlamp
  5. temperatureAfter cooling the reaction solution
  6. washwas washed sequentially with 5% aqueous sodium thiosulfate, dilute aqueous sodium bicarbonate, and 5% aqueous sodium thiosulfate
  7. dry with materialThe organic phase was dried (sodium sulfate)
  8. concentrationconcentrated
  9. customThe crude material was purified
  10. washeluting with 1:1 ethyl acetate-hexane
  11. customyielding 0.185 g (72%) of the title compund

Sources & evidence

ORD record
ord-5f54b3545f9f40e6b29cdae82297bb74
Source dataset
uspto-grants-1998_12
Patent number
US05843941

Reaction notes

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