1-(5-Chloro-2-fluorophenyl)propan-1-ol → 1-(5-Chloro-2-fluorophenyl)-1-propanone

HRID 1502398Notes

Reaction equation

HRID 1502398 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([CH:8]([OH:11])[CH2:9][CH3:10])[CH:7]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([C:8](=[O:11])[CH2:9][CH3:10])[CH:7]=1

Participants

4

Reactant 2

HCID 839883211-(5-Chloro-2-fluorophenyl)propan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 577900131-(5-Chloro-2-fluorophenyl)-1-propanoneYield 65.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1-(5-chloro-2-fluorophenyl)propan-1-ol (850 mg, 4.5 mmol) and pyridinium chlorochromate (1.7 g, 7.9 mmol) in methylene chloride (30 mL) was stirred at room temperature for 3 hours. The reaction mixture was diluted with methylene chloride (20 mL), filtered over Celite, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 12 g, ISCO, 0-30% ethyl acetate in heptane) to afford the title compound as a pale yellow oil (550 mg, 65%). 1H NMR (400 MHz, CDCl3) δ 7.38 (dd, J=8.8, 4.8 Hz, 1H), 7.16 (dd, J=8.3, 3.0 Hz, 1H), 7.09 (ddd, J=8.8, 7.7, 3.0 Hz, 1H), 2.95 (q, J=7.2 Hz, 2H), 1.21 (t, J=7.2 Hz, 3H).

Workup

  1. filtrationfiltered over Celite
  2. customevaporated in vacuo
  3. customto afford a residue that
  4. customwas purified by flash chromatography (silica, 12 g, ISCO, 0-30% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-c64e1daa2bf74a6b94719cf0ec80eea3
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

Loading…