N-bromobutanimide → HCID 12563003, compound

HRID 441675Notes

Reaction equation

HRID 441675 reaction equation
[C:1]([C:5]1[CH:21]=[CH:20][C:8]2[C:9](=[O:19])[C:10]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:11]=3[CH2:12][CH2:13][C:7]=2[CH:6]=1)([O:3]C)=[O:2].BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([C:5]1[CH:21]=[CH:20][C:8]2[C:9](=[O:19])[C:10]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:11]=3[CH:12]=[CH:13][C:7]=2[CH:6]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 21419714HCID 21419714, compound

Product 1

HCID 12563003HCID 12563003, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 1.49 g. of 2-carbomethoxy-9-fluoro-10,11-dihydro-5-oxo-5H-dibenzo[a,d]cycloheptene and 0.94 g. of N-bromosuccinimide in 100 ml of carbon tetrachloride was refluxed and irradiated with a 100 W incandescent lamp for 22 hours. The cooled solution was filtered and evaporated, and the residue dissolved in 25 ml of dimethylformamide. 1.5 Ml of diazabicyclononene was added and the mixture heated to 80° for 1 hours, then poured into dilute hydrochloric acid. The mixture was extracted with ethyl acetate and the extract washed, dried and evaporated. The residue was refluxed for 2 hours in 50 ml of water and 25 ml of methanol containing 1.5 g. of sodium hydroxide. The solution was cooled, acidified and filtered. The residue was recrystallized from aqueous dimethylformamide to yield 2-carboxy-9-fluoro-5-oxo-5H-dibenzo[a,d]cycloheptene, mp 340° (decomp.)

Workup

  1. customirradiated with a 100 W incandescent lamp for 22 hours
  2. filtrationThe cooled solution was filtered
  3. customevaporated
  4. dissolutionthe residue dissolved in 25 ml of dimethylformamide
  5. addition1.5 Ml of diazabicyclononene was added
  6. temperaturethe mixture heated to 80° for 1 hours
  7. additionpoured into dilute hydrochloric acid
  8. extractionThe mixture was extracted with ethyl acetate
  9. washthe extract washed
  10. customdried
  11. customevaporated
  12. temperatureThe residue was refluxed for 2 hours in 50 ml of water
  13. temperatureThe solution was cooled
  14. filtrationfiltered
  15. customThe residue was recrystallized from aqueous dimethylformamide

Sources & evidence

ORD record
ord-1d4ef37543834288bbb277fc204e2195
Source dataset
uspto-grants-1977_08
Patent number
US04041173

Reaction notes

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