Hydrochloric Acid → HCID 57655997, compound

HRID 911265Notes

Reaction equation

HRID 911265 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)=[O:4].Br[CH2:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl>CC(C)=O>[CH3:20][C:19]([CH3:22])([CH3:21])[C:18](=[O:23])[CH2:17][O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][NH:5][C:3](=[O:4])[C:2]([F:14])([F:15])[F:1])=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 21642BromopinacoloneHCID 57656322HCID 57656322, compound

Product 1

HCID 57655997HCID 57655997, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Mix 2,2,2-trifluoro-N-(4-hydroxy-benzyl)-acetamide (438 mg, 2.0 mmol), 1-bromopinacolone (430 mg, 2.4 mmol), anhydrous potassium carbonate (829 mg, 6.0 mmol) and potassium iodide (33 mg, 0.1 mmol) with acetone. Heat under reflux for 12 h. Acidify with 1N aqueous HCl and extract with EtOAc three times. Combine the organic extracts, wash with brine, dry over Na2SO4, filter and concentrate. Purify by chromatography on silica gel eluting with EtOAc/hexane (1:3) to give the desired intermediate as a colorless oil. MS (ES+) m/z: 335 (M+NH4)+. MS (ES−) m/z: 316 (M−H)−.

Workup

  1. temperatureHeat
  2. temperatureunder reflux for 12 h
  3. extractionextract with EtOAc three times
  4. washCombine the organic extracts, wash with brine
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify by chromatography on silica gel eluting with EtOAc/hexane (1:3)

Sources & evidence

ORD record
ord-594722e509654a47bd334db7da200e18
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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