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Triacetoxyperiodinane → 1-(4-Bromo-2-methylphenyl)-2,2,2-trifluoroethan-1-one

HRID 1499262
Notes
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Reaction equation

HRID 1499262 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[C:9]([F:12])([F:11])[F:10])=[C:4]([CH3:14])[CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[C:9]([F:11])([F:12])[F:10])=[C:4]([CH3:14])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 867673941-(4-Bromo-2-methylphenyl)-2,2,2-trifluoroethan-1-ol

Product 1

HCID 534028541-(4-Bromo-2-methylphenyl)-2,2,2-trifluoroethan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-bromo-2-methylphenyl)-2,2,2-trifluoroethanol (1.8 g, 6.7 mmol) in CH2Cl2 (20 mL) was added Dess-Martin Periodinane (3.4 g, 8.1 mmol) at 0° C. The mixture was stirred at RT for 2 h, then diluted with water (10 mL) and filtered. The filtrate was extracted with CH2Cl2. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by normal phase silica gel column provided 1-(4-bromo-2-methylphenyl)-2,2,2-trifluoroethanone as a yellow oil.

Workup

  1. filtrationfiltered
  2. extractionThe filtrate was extracted with CH2Cl2
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by normal phase silica gel column

Sources & evidence

ORD record
ord-fec117b12ef84e80862cdedd966aec89
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09199994B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes