Benzoyl Peroxide → HCID 53894245, compound

HRID 1679726Notes

Reaction equation

HRID 1679726 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][C:3]1([CH:21]([CH3:23])[CH3:22])[CH3:20].[Br:24]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH:4]([Br:24])[C:3]1([CH:21]([CH3:22])[CH3:23])[CH3:20]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 53744941HCID 53744941, compound

Product 1

HCID 53894245HCID 53894245, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of ethyl (1-oxo-2-isopropyl-2-methyl-6,7-dichloro-5-indanyloxy)acetate (3.6 g., 0.01 mole, N-bromosuccinimide (2.4 g., 0.0134 mole) and benzoyl peroxide (20 mg.) in carbon tetrachloride is refluxed 4 hours, cooled and filtered free of succinimide. The solvent is evaporated and the crude product is purified by column chromatography and then recrystallized from cyclohexane to afford substantially pure ethyl (1-oxo-2-isopropyl-2-methyl-3-bromo-6,7-dichloro-5-indanyloxy)acetate, m.p. 83°-85° C.

Workup

  1. temperaturecooled
  2. filtrationfiltered free of succinimide
  3. customThe solvent is evaporated
  4. customthe crude product is purified by column chromatography
  5. customrecrystallized from cyclohexane

Sources & evidence

ORD record
ord-7393e7fcc71440cf97c4ed256be7ead3
Source dataset
uspto-grants-1978_03
Patent number
US04081554

Reaction notes

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