N-bromobutanimide → 2-Bromomethyl-8-methyl-5H-dibenzo[a,d]cyclohepten-5-one

HRID 1275902Notes

Reaction equation

HRID 1275902 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6](=[O:16])[C:7]3[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:8]=3[CH:9]=[CH:10][C:4]=2[CH:3]=1.[Br:19]N1C(=O)CCC1=O>C(OCC)(=O)C>[Br:19][CH2:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6](=[O:16])[C:7]3[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:8]=3[CH:9]=[CH:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 221172592,8-dimethyl-5H-dibenzo[a,d][7]annulen-5-one

Product 1

HCID 221172722-Bromomethyl-8-methyl-5H-dibenzo[a,d]cyclohepten-5-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of step (i) (2.0 g) and N-bromosuccinimide (1.52 g) in ethyl acetate (80ml) was irradiated with a 500 W halogen lamp for 4 hours. The reaction mixture was washed with brine, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with toluene. Used directly in the next step.

Workup

  1. washThe reaction mixture was washed with brine
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. customPurification
  5. washeluting with toluene

Sources & evidence

ORD record
ord-4d603e7f5bba488d825ad0603cbf16b3
Source dataset
uspto-grants-2000_12
Patent number
US06162808

Reaction notes

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