N-bromobutanimide → HCID 23136352, compound

HRID 1678583Notes

Reaction equation

HRID 1678583 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.[Br:19]N1C(=O)CCC1=O>C1(C(F)(F)F)C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:19][CH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 23136528HCID 23136528, compound

Product 1

HCID 23136352HCID 23136352, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 7368(Trifluoromethyl)benzeneSolvent

Conditions

Temperature
100 °C

Procedure

1-(3-Methylphenoxy)naphthalene (500 mg, 2.1 mmol) was dissolved in benzotrifluoride (30 mL), N-bromosuccinimide (417 mg, 2.3 mmol) and 2,2′-azobis(isobutyronitrile) (10 mg, 0.06 mmol) were added thereto, and then the mixture was stirred at 100° C. for 4 hours. The reaction solution was filtered, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=100:0 to 90:10) to give the title compound (481 mg, yield 73%).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=100:0 to 90:10)

Sources & evidence

ORD record
ord-51593668d15240359f448e039e59377a
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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