HCID 67266122, compound → HCID 57816586, compound

HRID 1684864Notes

Reaction equation

HRID 1684864 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([OH:27])[CH2:20][CH2:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:15][CH:14]=1>ClCCl>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:27])[CH2:20][CH2:21][CH2:22][C:23]([F:25])([F:26])[F:24])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 67266122HCID 67266122, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 57816586HCID 57816586, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PCC (9.29 g, 43.1 mmol) was admixed with 9 g SiO2 and ground with mortar & pestle before being added in one portion to a solution of 1-(4-bromophenyl)-5,5,5-trifluoropentan-1-ol (6.4 g, 21.54 mmol) dissolved in dichloromethane (350 mL). The reaction was stirred 4 h, filtered through diatomaceous earth (Celite®), concentrated, and applied to a 160 g Thomson® silica gel column. Elution: 10-60% B over 1.5 L (A/B Hexanes/EtOAc) gave Example 5b, 1-(4-bromophenyl)-5,5,5-trifluoropentan-1-one 6.1 g (86%). 1H NMR (500 MHz, CDCl3) δ 7.81 (d, J=8.5 Hz, 2H), 7.61 (d, J=8.3 Hz, 2H), 3.04 (t, J=7.0 Hz, 2H), 2.25-2.16 (m, 2H), 2.05-1.99 (m, 2H). RT=2.1 minutes (condition 1). LCMS: Anal. Calcd. For C11H11BrF3O: 295.00. found: 295.00 (M+H).

Workup

  1. filtrationfiltered through diatomaceous earth (Celite®)
  2. concentrationconcentrated
  3. washElution

Sources & evidence

ORD record
ord-8558c15d5fa247008829cf3c9c23aa03
Source dataset
uspto-grants-2012_04
Patent number
US08147818B2

Reaction notes

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