N-bromobutanimide → HCID 14835362, compound

HRID 1198994Notes

Reaction equation

HRID 1198994 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][N:10]=[C:11]3[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=23)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:18][CH2:17][C:16]1[C:11]2[C:12](=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[O:9][N:10]=2)[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 14835361HCID 14835361, compound

Product 1

HCID 14835362HCID 14835362, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 9.7 g (0.0427 mole) of 3-(4-fluorophenyl)-7-methyl-2,1-benzisoxazole, 7.7 g (0.0431 mole) of N-bromosuccinimide and 0.2 g of dibenzoyl peroxide in 300 ml of carbon tetrachloride was heated at reflux under floodlight illumination and under an argon atmosphere for 3.5 hr. The cooled reaction mixture was filtered and the filtrate was concentrated under reduced pressure to give 10.4 g of solid. The solid was recrystallized twice from 2-propanol to give 9.0 g (69%) of light-yellow, fluffy needles, m.p. 145°-148° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under floodlight illumination and under an argon atmosphere for 3.5 hr
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0a59eb37de614a9989dfd80307505938
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

Loading…