Bromine → HCID 22105454, compound

HRID 358045Notes

Reaction equation

HRID 358045 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][CH2:8][CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:6]=2[CH:20]=1.BrBr>C(Cl)(Cl)(Cl)Cl>[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

Participants

4

Reactant 2

HCID 24408BromineHCID 20449988HCID 20449988, compound

Product 1

HCID 22105454HCID 22105454, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of 10.25 g of 7-chloro-5-(2-fluorophenyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in 880 ml of carbon tetrachloride is treated with 4.5 ml of bromine and heated to boiling while stirring for 2 hours while irradiating with a 500 W incandescent lamp. The solution is evaporated in vacuo. The residue is dissolved in 880 ml of 2 propanol and hydrogenated at room temperature and normal pressure in the presence of 1.3 g of palladium-on-carbon (5%). The catalyst is filtered off and the filtrate is evaporated. The residue is dissolved in benzene and chromatographed on 295 g of silica gel. Impurities and starting material are eluted with benzene/ethyl acetate (29:1) and the desired product is eluted with benzene/ethyl acetate (19:1). After recrystallization from benzene/ether, there is obtained 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1-benzazepin-2-one of melting point 214°-215°.

Workup

  1. temperatureheated
  2. customwhile irradiating with a 500 W incandescent lamp
  3. customThe solution is evaporated in vacuo
  4. dissolutionThe residue is dissolved in 880 ml of 2 propanol and hydrogenated at room temperature
  5. filtrationThe catalyst is filtered off
  6. customthe filtrate is evaporated
  7. dissolutionThe residue is dissolved in benzene
  8. customchromatographed on 295 g of silica gel
  9. washare eluted with benzene/ethyl acetate (29:1)
  10. washthe desired product is eluted with benzene/ethyl acetate (19:1)
  11. customAfter recrystallization from benzene/ether

Sources & evidence

ORD record
ord-fd50aca8ac42475f91ba9da37aef7f48
Source dataset
uspto-grants-1984_08
Patent number
US04464300

Reaction notes

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