N-bromobutanimide → HCID 12274177, compound

HRID 1198618Notes

Reaction equation

HRID 1198618 reaction equation
[CH3:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:16])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:17][CH2:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:16])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 2196654-Methylxanthen-9-one

Product 1

HCID 12274177HCID 12274177, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A well-stirred mixture of the above 4-methylxanthenone (6.5 g, 31 mmol), N-bromosuccinimide (5.5 g, 31 mmol) and benzoyl peroxide (30 mg) in dry CCl4 (250 mL) was heated under reflux with powerful illumination for 3 h. The hot mixture was filtered, the filtrate was evaporated and the residue was crystallized from the minimum volume of boiling petroleum ether (ca. 1800 mL) to give 4-bromomethylxanthenone (VII: R1 =H, Z=CH2Br) (6.3 g, 71%) as colourless needles, mp 191°-192° C. Anal. (C14H9BrO2) C,H,N,Br.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux with powerful illumination for 3 h
  3. filtrationThe hot mixture was filtered
  4. customthe filtrate was evaporated
  5. customthe residue was crystallized from the minimum volume of boiling petroleum ether (ca. 1800 mL)

Sources & evidence

ORD record
ord-b24c146991404dfa8fe91e716481cfbb
Source dataset
uspto-grants-1994_01
Patent number
US05281620

Reaction notes

Loading…