Potassium Bromide → 2,2,2-Trifluoro-1-(2-fluoro-5-(4-fluorobenzoyl)phenyl)ethanone

HRID 928769Notes

Reaction equation

HRID 928769 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([C:5]1[CH:10]=[C:9]([CH:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[OH:12])[CH:8]=[CH:7][C:6]=1[F:20])=[O:4].CC1(C)N([O])C(C)(C)CCC1.[K+].[Br-].C([O-])(O)=O.[Na+].[O-]Cl.[Na+]>C(Cl)Cl>[F:22][C:2]([F:1])([F:21])[C:3]([C:5]1[CH:10]=[C:9]([C:11](=[O:12])[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:8]=[CH:7][C:6]=1[F:20])=[O:4]

Participants

7

Reactant 5

HCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 23665760Sodium HypochloriteHCID 867156112,2,2-Trifluoro-1-(2-fluoro-5-((4-fluorophenyl)(hydroxy)methyl)phenyl)ethanone2×

Product 1

HCID 867156122,2,2-Trifluoro-1-(2-fluoro-5-(4-fluorobenzoyl)phenyl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A homogeneous yellow solution of crude 2,2,2-trifluoro-1-(2-fluoro-5-((4-fluorophenyl)(hydroxy)methyl)phenyl)ethanone (1.15 g, 3.64 mmol, Intermediate 35: step b) and TEMPO (18.4 mg, 0.118 mmol) in DCM (7.3 mL) was stirred on an ice bath while a solution of aqueous KBr (43 mg, 0.36 mmol) in 1 M aqueous NaHCO3 (1.27 mL, 1.27 mmol) was added in one portion. NaOCl [4.6 mL, 0.89 M (6.15% w/w Clorox bleach), 4.1 mmol] was then added dropwise over 5 minutes to the homogeneous bilayer. After 20 minutes stirring on the ice bath, the clear yellow organic layer was collected, and the aqueous layer extracted with DCM (1×6 mL). The combined organic layers were washed with 5 M aqueous NaCl (1×3 mL), dried (Na2SO4), filtered, and concentrated to provide the crude title compound as a clear yellow oil.

Workup

  1. additionwas added in one portion
  2. customthe clear yellow organic layer was collected
  3. extractionthe aqueous layer extracted with DCM (1×6 mL)
  4. washThe combined organic layers were washed with 5 M aqueous NaCl (1×3 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c8535f56bffc4d8784ebdec1208cce36
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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