Sodium hydride → HCID 86710508, compound

HRID 1849982Notes

Reaction equation

HRID 1849982 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:19])=[C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[O:11])[CH:9]=1.[C:20]([CH2:24]OS(C(F)(F)F)(=O)=O)([F:23])([F:22])[F:21].[NH4+].[Cl-]>CN(C=O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:19])=[C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:24][C:20]([F:23])([F:22])[F:21])=[CH:14][CH:13]=2)=[O:11])[CH:9]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 66582827HCID 66582827, compound

Product 1

HCID 86710508HCID 86710508, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At 0° C., NaH (1.6 g) was added into a solution of (5-bromo-2-chlorophenyl)(4-hydroxyphenyl)methanone (6.2 g) in dry DMF (40 mL). The mixture was stirred at room temperature for 1 h. Then CF3CH2OTf (9.3 g) was slowly added into the mixture at 0° C. The mixture was stirred at room temperature for 0.5 h. Saturated NH4Cl aqueous solution was added slowly into the mixture, and the mixture was extracted with EtOAc. The organic phases were combined, dried over Na2SO4 and concentrated to obtain the crude product, then the crude product was purified by silica-gel column chromatography (PE/EA=20/1) to obtain 5.0 g of (5-bromo-2-chlorophenyl)(4-(2,2,2-trifluoroethoxy)phenyl)methanone.

Workup

  1. stirringThe mixture was stirred at room temperature for 0.5 h
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto obtain the crude product
  6. customthe crude product was purified by silica-gel column chromatography (PE/EA=20/1)

Sources & evidence

ORD record
ord-378eba0574704947aece7541954c7f13
Source dataset
uspto-grants-2015_02
Patent number
US08957033B2

Reaction notes

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