Diethyl Ether → 2,2,2-Trifluoro-1-(2-methoxyphenyl)ethanone

HRID 859647Notes

Reaction equation

HRID 859647 reaction equation
CO[Mg][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br-].[F:11][C:12]([F:18])([F:17])[C:13](OC)=[O:14].[CH2:19]([O:21]CC)C>>[F:11][C:12]([F:18])([F:17])[C:13]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=1[O:21][CH3:19])=[O:14]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 9893Methyl trifluoroacetateHCID 178502596HCID 178502596, compound

Product 1

HCID 27597332,2,2-Trifluoro-1-(2-methoxyphenyl)ethanone

Procedure

2 Methoxy phenyl magnesium bromide (35 ml) was added slowly to a solution of methyl trifluoroacetate (5.0 g) in diethyl ether (100 ml) at −78° C. The reaction mixture was warmed to room temperature over 12 hrs and the quenched with saturated ammonium chloride solution (100 ml). The mixture was then partitioned between ethyl acetate (500 ml) and water (250 ml) The organics were separated and dried over magnesium sulfate filtered and concentrated in vacuuo. The crude residue was purified by column chromatography on silica gel eluting with 100% hexanes, 90:10 and 80:20, hexanes:ethyl acetate, to afford title compound as a yellow oil. (4.0 g). 1H NMR (CDCl3): δ 3.57 (s, 3 H), 7.00 (m, 2 H), 7.35 (m,1 H), 7.63, (d, J=2.54 Hz 2 H).

Workup

  1. customthe quenched with saturated ammonium chloride solution (100 ml)
  2. customThe mixture was then partitioned between ethyl acetate (500 ml) and water (250 ml) The
  3. customorganics were separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuuo
  7. customThe crude residue was purified by column chromatography on silica gel eluting with 100% hexanes, 90:10 and 80:20, hexanes

Sources & evidence

ORD record
ord-87479ca1feac4387aabc3c0ba1f394da
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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