Benzoyl Peroxide → HCID 4534807, compound

HRID 2071713Notes

Reaction equation

HRID 2071713 reaction equation
[CH:1](=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=[CH:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2)[CH3:2].[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:2][CH:1]=[C:3]1[C:4]2[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=2[CH:6]=[CH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 22416519HCID 22416519, compound

Product 1

HCID 4534807HCID 4534807, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-ethylidene-5H-dibenzo[a,d]cycloheptene (10.9 g., 0.05 mole), N-bromosuccinimide (8.9 g., 0.05 mole), benzoyl peroxide (15 mg.) and 150 ml. of carbon tetrachloride is stirred and heated to refluxing on the steam-bath for 4 hours. After cooling, the succinimide is separated by filtration and washed with carbon tetrachloride. The combined filtrate and washings are evaporated to dryness under reduced pressure. Crystallization of the residual solid from petroleum ether gave 5-(2-bromoethylidene)-5H-dibenzo[a,d]cycloheptene in a yield of 10.65 g. (72%), m.p. 87.5°-89.5° C. An analytical sample, after recrystallization from petroleum ether, melted at 80°-90° C.

Workup

  1. temperatureheated
  2. temperatureto refluxing on the steam-bath for 4 hours
  3. temperatureAfter cooling
  4. customthe succinimide is separated by filtration
  5. washwashed with carbon tetrachloride
  6. customThe combined filtrate and washings are evaporated to dryness under reduced pressure
  7. customCrystallization of the residual solid from petroleum ether

Sources & evidence

ORD record
ord-8893c7725fab4194ab7352b39ac66e42
Source dataset
uspto-grants-1977_09
Patent number
US04048223

Reaction notes

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