Benzoyl Peroxide → HCID 58073801, compound

HRID 1470582Notes

Reaction equation

HRID 1470582 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:17][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 58073894HCID 58073894, compound

Product 1

HCID 58073801HCID 58073801, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-fluoro-3′-methoxy-4-methyl-bipheny (0.5 g, 1.7 mmol, 1.0 eq) in chloroform (30 mL), was added N-bromo succinimide (0.3 g, 1.7 mmol followed by catalytic amount of dibenzoyl peroxide. The reaction mixture was refluxed by irradiating with a tungsten lamp for 3 hours. After the reaction was completed, it was cooled to room temperature and washed with water. The combined organic layers were dried over anhydrous sodium sulphate and concentrated. The resulting residue was purified by column chromatography using 5% ethyl acetate in hexane to obtain the title compound (0.45 g, 89%).

Workup

  1. temperatureThe reaction mixture was refluxed
  2. customby irradiating with a tungsten lamp for 3 hours
  3. washwashed with water
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-b40bc2371aae4c8facda606e09dab80c
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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