N-bromobutanimide → HCID 14350666, compound

HRID 2291535Notes

Reaction equation

HRID 2291535 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH3:17])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:18][CH2:19][CH3:20])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:21])[CH:5]=1.[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:22][CH:10]1[C:9]2([CH2:18][CH2:19][CH3:20])[C:4](=[CH:5][C:6](=[O:21])[CH2:7][CH2:8]2)[C:3]2[C:11]1=[CH:12][C:13]([O:16][CH3:17])=[C:14]([Cl:15])[C:2]=2[Cl:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 13613331HCID 13613331, compound

Product 1

HCID 14350666HCID 14350666, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5,6-dichloro-1,2,9,9a-tetrahydro-7-methoxy-9a-propyl-3H-fluoren-3-one (3.25 g, 0.01 mol), N-bromosuccinimide (1.78 g, 0.01 mole) and benzoyl peroxide (75 mg) in carbon tetrachloride (50 ml) was heated at reflux for 13/4 hours, cooled, filtered and the CCl4 distilled at reduced pressure to give 3.70 g 9-bromo-5,6-dichloro-7-methoxy-9a-propyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one which melted at 131.5°-133.5° C. after crystallization from diethyl ether.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 13/4 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. distillationthe CCl4 distilled at reduced pressure

Sources & evidence

ORD record
ord-d246a5e8d5964a50b5544b3e62d6e3f6
Source dataset
uspto-grants-1989_01
Patent number
US04797391

Reaction notes

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