Methyl trifluoroacetate → 1-(4-Chloro-3,5-difluorophenyl)-2,2,2-trifluoroethanone

HRID 1258014Notes

Reaction equation

HRID 1258014 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:10])[C:5]([Cl:9])=[C:6]([F:8])[CH:7]=1.C([Mg]Cl)(C)C.[Li+].[Cl-].[F:18][C:19]([F:25])([F:24])[C:20](OC)=[O:21]>C1COCC1>[Cl:9][C:5]1[C:4]([F:10])=[CH:3][C:2]([C:20](=[O:21])[C:19]([F:25])([F:24])[F:18])=[CH:7][C:6]=1[F:8]

Participants

5

Reactant 3

HCID 9893Methyl trifluoroacetateHCID 27732585-Bromo-2-chloro-1,3-difluorobenzeneHCID 178461733HCID 178461733, compound

Product 1

HCID 866705371-(4-Chloro-3,5-difluorophenyl)-2,2,2-trifluoroethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-bromo-2-chloro-1,3-difluorobenzene (2000 mg, 8.2 mmol) was stirred at room temperature in THF under N2 and the isopropylmagnesium chloride/LiCl reagent (1310 mg, 9.02 mmol, 6.94 mL) was added over about 1 minute—very slight exotherm noticed to ˜30° C. Reaction was stirred at room temperature for 30 minutes followed by the addition of methyl trifluoroacetate (1580 mg, 12.3 mmol, 1.24 mL) over about 1 minute—slight exotherm to ˜40° C. Solvents were evaporated under reduced pressure to provide the desired product. 1H NMR (CDCl3) δ ppm: 8.05 (s, 2H).

Workup

  1. customnoticed to ˜30° C
  2. customReaction
  3. customSolvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-7b87c04eeff14325a6efc855e0676636
Source dataset
uspto-grants-2013_06
Patent number
US08466115B2

Reaction notes

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