Benzoyl Peroxide → HCID 15614962, compound

HRID 1088550Notes

Reaction equation

HRID 1088550 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:42][CH3:43])[C:34]=2[C:38]([F:41])([F:40])[F:39])[C:29]=1[CH3:44]>C(Cl)(Cl)(Cl)Cl>[Br:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:42][CH3:43])[C:34]=2[C:38]([F:40])([F:41])[F:39])[C:29]=1[CH2:44][Br:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 15614963HCID 15614963, compound

Product 1

HCID 15614962HCID 15614962, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (21.07 g, 1.5 eq) and benzoyl peroxide (84 mg, 0.0044 eq) were added to a stirred solution of 2-bromo-6-methoxy-1-methyl-5-trifluoromethylnaphthalene (25.19 g, 78.9 mmol, prepared by the process of Example 17, Step 1) in carbon tetrachloride (300 mL) at room temperature under a dry nitrogen atmosphere. The reaction was heated to reflux for 6 hours, then cooled to ~50° C. The warm reaction mixture was filtered. The solid was washed with warm carbon tetrachloride (2×30 mL). The carbon tetrachloride was removed from the filtrate to provide the light yellow solid (32.4 g, 100%), m.p. 141.5-143° C.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 6 hours
  3. temperaturecooled to ~50° C
  4. customThe warm reaction mixture
  5. filtrationwas filtered
  6. washThe solid was washed with warm carbon tetrachloride (2×30 mL)
  7. customThe carbon tetrachloride was removed from the filtrate

Sources & evidence

ORD record
ord-877cab2579894fb5b5bf7228009027f8
Source dataset
uspto-grants-1990_10
Patent number
US04962224

Reaction notes

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