Hydrochloric Acid → 1-(2-Bromo-4-fluorophenyl)-2,2-difluoroethan-1-one

HRID 558125Notes

Reaction equation

HRID 558125 reaction equation
[Li]CCCC.[Br:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1I.[F:15][CH:16]([F:22])[C:17](OCC)=[O:18].Cl>C1COCC1>[Br:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:17](=[O:18])[CH:16]([F:22])[F:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9961Ethyl difluoroacetateHCID 27733722-Bromo-4-fluoro-1-iodobenzeneHCID 178418339Butyllithium

Product 1

HCID 574450751-(2-Bromo-4-fluorophenyl)-2,2-difluoroethan-1-oneYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add n-BuLi (8.86 mL, 14.18 mmol) slowly to a solution of 2-bromo-4-fluoro-1-iodobenzene (4.27 g, 14.2 mmol) in THF (50 mL) at −100° C. over 15 min under N2. Stir the solution for 30 min. Add ethyl difluoroacetate (2.81 mL, 26.9 mmol) and stir for 3 h. Add an HCl (50 mL, 2 N) solution and warm the solution up to RT. Separate the organic layer, dry the organic layer over magnesium sulfate, and remove the solvent. Purify the residue by column chromatography (hexane:ethyl acetate/10:1) to give the title compound (2.3 g, 64%). MS (GC) m/z 252 [M]+.

Workup

  1. customSeparate the organic layer
  2. dry with materialdry the organic layer over magnesium sulfate
  3. customremove the solvent
  4. customPurify the residue by column chromatography (hexane:ethyl acetate/10:1)

Sources & evidence

ORD record
ord-2da8265ffca44b6193a090cd59854996
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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