N-bromobutanimide → HCID 21706515, compound

HRID 1005390Notes

Reaction equation

HRID 1005390 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:17])([CH3:16])[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:10])=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:18][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:16])([CH3:17])[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 21706499HCID 21706499, compound

Product 1

HCID 21706515HCID 21706515, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of t butyl 2-(4-methylphenyl)-2,2-dimethylacetate (19.4 g, 83 mmol) in carbon tetrachloride (350 mL) was added N-bromosuccinimide (16.2 g, 92 mmol) and benzoyl peroxide (0.5 g). The mixture was heated under reflux for 1 hour. The mixture was cooled to rt, and the precipitate was removed by filtration. The filtrate was washed with 10% NaHCO3 and brine, dried (Na2SO4), and evaporated to give t butyl 2-(4-bromomethylphenyl)-2,2-dimethylacetate as a light yellow oil (26.4 g, 100%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customthe precipitate was removed by filtration
  4. washThe filtrate was washed with 10% NaHCO3 and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-3b515cc34f254de7be4ab24619cc45f5
Source dataset
uspto-grants-2000_04
Patent number
US06054470

Reaction notes

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