N-bromobutanimide → HCID 58296104, compound

HRID 2189495Notes

Reaction equation

HRID 2189495 reaction equation
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1.[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:18][CH:10]([C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:16])([F:17])[F:1])=[CH:9][CH:8]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67219206HCID 67219206, compound

Product 1

HCID 58296104HCID 58296104, compoundYield 103.2%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of ethyl 2-(4-(trifluoromethoxy)phenyl)acetate (1.99 g, 8.00 mmol), N-bromosuccinimide (NBS) (1.57 g, 8.80 mmol) and 2,2′-azobis(2-methylpropionitrile) (AIBN) (66 mg, 0.400 mmol) in carbon tetrachloride (10 ml) was heated under reflux for 5 hours. The reaction mixture was concentrated in vacuo, diluted with diethyl ether (200 ml), washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo to give ethyl 2-bromo-2-(4-(trifluoromethoxy)phenyl)acetate (65) (2.70 g, quantitative yield) as yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additiondiluted with diethyl ether (200 ml)
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9892a53e21694c90831b0c320a44b269
Source dataset
uspto-grants-2012_12
Patent number
US08324249B2

Reaction notes

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