N-bromobutanimide → HCID 20082001, compound

HRID 1609602Notes

Reaction equation

HRID 1609602 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:17]=[C:16]3[C:10]([CH2:11][CH2:12][O:13][C:14]3=[O:15])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:17]=[C:16]3[C:10]([CH:11]=[CH:12][O:13][C:14]3=[O:15])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 200820007-(4-Chlorophenoxy)-3,4-dihydroisocoumarin

Product 1

HCID 20082001HCID 20082001, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 500 mg of 7-(4-chlorophenoxy)-3,4-dihydroisocoumarin, 325 mg of N-bromosuccinimide and 20 mg of benzoyl peroxide in 20 ml of carbon tetrachloride was refluxed under heating for 2 hours. After finishing the reaction, the mixture was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was mixed with 10 ml of toluene and 490 mg of 1,8-diazabicyclo[5, 4, 0]undec-7-ene and stirred at room temperature for 1 hour. The toluene was evaporated in vacuo, and the resultant residue was chromatographed on a column of silica gel, eluting with ethyl acetate and hexane (1:1) to give 367 mg of the titled compound.

Workup

  1. temperatureunder heating for 2 hours
  2. customthe reaction
  3. washthe mixture was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. additionThe resultant residue was mixed with 10 ml of toluene and 490 mg of 1,8-diazabicyclo[5, 4, 0]undec-7-ene
  7. customThe toluene was evaporated in vacuo
  8. customthe resultant residue was chromatographed on a column of silica gel
  9. washeluting with ethyl acetate and hexane (1:1)

Sources & evidence

ORD record
ord-d4959f0808cf473d882b26843b5d4a52
Source dataset
uspto-grants-1995_03
Patent number
US05401756

Reaction notes

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