Benzoyl Peroxide → HCID 18319327, compound

HRID 1700867Notes

Reaction equation

HRID 1700867 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH:27]1([O:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[C:35]([CH3:40])[CH:34]=2)[CH2:31][CH2:30][CH2:29][CH2:28]1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][CH2:40][C:35]1[CH:34]=[C:33]([O:32][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[CH:38]=[CH:37][C:36]=1[F:39]

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide2×HCID 18319330HCID 18319330, compound

Product 1

HCID 18319327HCID 18319327, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

4.81 g of N-bromosuccinimide (27 mmol) and 0.6 g of benzoyl peroxide (2 mmol) are introduced into a solution of 5 g of 4-cyclopentyloxy-1-fluoro-2-methylbenzene (25.8 mmol) in carbon tetrachloride (130 ml). The mixture is heated at 80° C. for 17 hours, a further 2.29 g of N-bromosuccinimide (12.89 mmol) and 0.3 g of benzoyl peroxide (1 mmol) are then added and heating is continued for 12 hours. The mixture is then cooled to room temperature and filtered through Celite. The mother liquor is concentrated and the black oil obtained is purified by chromatography on a column of silica (eluent: 88/12 cyclohexane/ethyl acetate). 4.63 g of an orange oil are obtained:

Workup

  1. temperatureheating
  2. temperatureThe mixture is then cooled to room temperature
  3. filtrationfiltered through Celite
  4. concentrationThe mother liquor is concentrated
  5. customthe black oil obtained
  6. customis purified by chromatography on a column of silica (eluent: 88/12 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-343f356d6c774de8883fa24ad77fe10b
Source dataset
uspto-grants-2002_02
Patent number
US06350913B1

Reaction notes

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