Triethylamine → 2-Fluoro-1-(2-fluoro-phenyl)-ethanone

HRID 876375Notes

Reaction equation

HRID 876375 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:11])[CH2:9]O.C(N(CC)CC)C.F.F.F.C(N(CC)CC)C.[F:29]C(F)(C(F)(F)F)C(F)(F)C(F)(F)S(F)(=O)=O.C(=O)([O-])O.[Na+]>ClCCl>[F:29][CH2:9][C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])=[O:11]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 516892Sodium BicarbonateHCID 21837678HCID 21837678, compound

Product 1

HCID 219644912-Fluoro-1-(2-fluoro-phenyl)-ethanoneYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(2-fluorophenyl)-2-hydroxyethanone [CAS 218771-68-7; WO9857925, ex. 16) (2.77 g, 18.0 mmol) in dichloromethane (42 ml) was treated consecutively at 0° C. with triethylamine (6.36 g, 62.8 mmol), triethylamine trihydrofluoride (3.05 g, 18.0 mmol) and nonafluoro-n-butanesulfonyl fluoride (8.48 g, 26.9 mmol). The tube was sealed and the reaction mixture stirred overnight at room temperature. For the workup, the dark red solution was poured on a saturated solution of sodium hydrogencarbonate and ice, then extracted with dichloromethane. The organic layer was separated, dried over sodium sulphate and evaporated. The crude material was purified by flash chromatography on silica gel (Telos Flash Silica) using dichloromethane as the eluent to give the 2-fluoro-1-(2-fluoro-phenyl)-ethanone (1.23 g, 61% yield) as a yellow semisolid.

Workup

  1. customThe tube was sealed
  2. extractionextracted with dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe crude material was purified by flash chromatography on silica gel (Telos Flash Silica)

Sources & evidence

ORD record
ord-58ba0cfb4d7a49438f29a8ede9b4c0ff
Source dataset
uspto-grants-2015_03
Patent number
US08987255B2

Reaction notes

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