Hydrogen Bromide → HCID 59597449, compound

HRID 2265075Notes

Reaction equation

HRID 2265075 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1.[C:16](Cl)(=O)C(Cl)=O.C(Cl)(Cl)(Cl)Cl.C1C(=O)N(Br)C(=O)C1.[BrH:35]>CN(C=O)C.CO>[Br:35][CH:10]([C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:14])([F:15])[F:1])=[CH:9][CH:8]=1)[C:11]([O:13][CH3:16])=[O:12]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 67184N-bromobutanimideHCID 27773192-[4-(Trifluoromethoxy)phenyl]acetic acidHCID 86613164HCID 86613164, compound

Product 1

HCID 59597449HCID 59597449, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-trifluoromethoxyphenylacetic acid (5 g, 23 mmol) in carbon tetrachloride oxalyl chloride (25 mmol) and two drops of DMF were added at 0° C. After stirring the solution at room temperature for 1 h, NBS (25 mmol) and few drops of 48% HBr were added and the mixture was heated to reflux for 4 h. The solution was allowed to cool, MeOH (5 mL) was added and the mixture was stirred at room temperature for 1 h. After filtration through a pad of silica gel, the filtrate was evaporated in vacuo to give 7.2 g of the title compound as yellow foam, which was used in the subsequent step without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 h
  3. temperatureto cool
  4. stirringthe mixture was stirred at room temperature for 1 h
  5. filtrationAfter filtration through a pad of silica gel
  6. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-e9754dc7cb2f4d33a76263054dd988f5
Source dataset
uspto-grants-2010_12
Patent number
US07855298B2

Reaction notes

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