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

HRID 634800Notes

Reaction equation

HRID 634800 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-55d16c958f394beb8e9d507948fa47c6
Source dataset
uspto-grants-2001_02
Patent number
US06184242B2

Reaction notes

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