N-bromobutanimide → 4-Bromomethyl-4'-nitrobenzophenone

HRID 2121025Notes

Reaction equation

HRID 2121025 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:19][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[O:7])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 2191314-Methyl-4'-nitrobenzophenone

Product 1

HCID 143775484-Bromomethyl-4'-nitrobenzophenoneYield 112.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Benzoyl peroxide (0.012 g) was added to a mixture of 4-(4-methylbenzoyl)-nitrobenzene (1.20 g) and N-bromosuccinimide (0.89 g) suspended in carbon tetrachloride (63 mL). The reaction mixture was refluxed under argon for 4 hours while illuminated with an incandescent lamp. The mixture was filtered, and the yellow solution containing the crude product was evaporated, chromatographed on silica gel, eluting with hexane/ethyl acetate, to give 4-(4-bromomethylbenzoyl)-nitrobenzene (1.79 g, 81%) as a white solid, m.p. 112.7-113.1° C.

Workup

  1. temperatureThe reaction mixture was refluxed under argon for 4 hours
  2. customwhile illuminated with an incandescent lamp
  3. filtrationThe mixture was filtered
  4. additionthe yellow solution containing the crude product
  5. customwas evaporated
  6. customchromatographed on silica gel
  7. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-559ad4b3a4c34784a08c08a85d41f9c7
Source dataset
uspto-grants-2004_02
Patent number
US06693200B2

Reaction notes

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