N-bromobutanimide → HCID 13621300, compound

HRID 464743Notes

Reaction equation

HRID 464743 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][Br:16])[C:10]=1[CH2:17][Br:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[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>[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([Br:19])[Br:16])[C:10]=1[CH2:17][Br:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 20262459HCID 20262459, compound

Product 1

HCID 13621300HCID 13621300, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

1-Benzoyl-2,3-bis(bromomethyl)benzene (8.0 g, 22 mmol) (crude, Description 7) was dissolved in carbon tetrachloride (50 ml) and recrystallized N-bromosuccinimide (3.9 g 22 mmol) and dibenzoyl peroxide (100 mg) were added. The mixture was heated to reflux for sixteen hours, cooled and filtered. The solid was washed with carbon tetrachloride (2×10 ml) and the combined organic layers were evaporated under reduced pressure to give crude 1-benzoyl-2-bromomethyl-3-(dibromomethyl)benzene (9.0 g, 93% recovery).

Workup

  1. additionwere added
  2. temperatureThe mixture was heated
  3. temperatureto reflux for sixteen hours
  4. temperaturecooled
  5. filtrationfiltered
  6. washThe solid was washed with carbon tetrachloride (2×10 ml)
  7. customthe combined organic layers were evaporated under reduced pressure

Sources & evidence

ORD record
ord-f7205662d3554bdfaedd10c8df7a35c9
Source dataset
uspto-grants-1985_10
Patent number
US04548948

Reaction notes

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