Bromobenzene → HCID 13592863, compound

HRID 1520298Notes

Reaction equation

HRID 1520298 reaction equation
[F:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][C:5](O)=[O:6].C(Cl)(=O)C(Cl)=O.[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl-].[Al+3].[Cl-].[Cl-]>O.CN(C=O)C>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([CH:5]([OH:6])[CH2:4][CH2:3][C:2]([F:9])([F:8])[F:1])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 7961BromobenzeneHCID 65578Oxalyl chlorideHCID 27770854,4,4-Trifluorobutanoic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13592863HCID 13592863, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4,4,4-trifluorobutanoic acid (1.0 g), oxalyl dichloride (0.820 mL) and bromobenzene (3.71 mL) was added DMF (0.008 mL), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added aluminum chloride (1.408 g) at 0° C., and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added water at 0° C., the mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. To a mixture of the residue, ethanol (15 mL) and THF (5 mL) was added sodium borohydride (0.266 g) at 0° C., and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added water at 0° C., the mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.49 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionTo a mixture of the residue, ethanol (15 mL) and THF (5 mL)
  7. additionwas added sodium borohydride (0.266 g) at 0° C.
  8. stirringthe mixture was stirred at room temperature for 2 hr
  9. additionTo the reaction mixture was added water at 0° C.
  10. extractionthe mixture was extracted with ethyl acetate
  11. washthe extract was washed with water and saturated brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThe solvent was evaporated under reduced pressure
  14. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-310a3c8012014e3192123217d06eb089
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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