Ethyl fluoroacetate → HCID 86679081, compound

HRID 1039356Notes

Reaction equation

HRID 1039356 reaction equation
[F:1][CH2:2][C:3]([O:5]CC)=O.[Cl:8][C:9]1[CH:18]=[CH:17][C:12]([CH2:13][CH2:14][Mg]Br)=[CH:11][CH:10]=1>O1CCCC1.[Cl-].[NH4+]>[Cl:8][C:9]1[CH:18]=[CH:17][C:12]([CH2:13][CH2:14][C:3](=[O:5])[CH2:2][F:1])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 9988Ethyl fluoroacetateHCID 178478085HCID 178478085, compound

Product 1

HCID 86679081HCID 86679081, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
-50 °C

Procedure

To a stirred solution of ethyl fluoroacetate (0.59 ml; 6.0 mmol) in tetrahydrofuran (6 ml) under nitrogen at −76° C. was added dropwise a 0.5 M solution of 4-chlorophenethylmagnesium bromide in tetrahydrofuran (10 ml; 5.0 mmol). The suspension obtained was stirred at −50° C. during 5 h. The mixture was poured in ammonium chloride sat. solution (20 ml) and extracted with dichloromethane (3×20 ml). Combined organics were dried over sodium sulfate and evaporated. The crude obtained was subject flash chromatography (eluant: c-hexane/ethyl acetate 95:5) to afford 0.13 g (18% of theory) of 4-(4-chloro-phenyl)-1-fluoro-butan-2-one as a yellow oil.

Workup

  1. customThe suspension obtained
  2. extractionextracted with dichloromethane (3×20 ml)
  3. dry with materialCombined organics were dried over sodium sulfate
  4. customevaporated
  5. customThe crude obtained

Sources & evidence

ORD record
ord-7dd15a52eb164afb8f382c2c4b938486
Source dataset
uspto-grants-2013_10
Patent number
US08552049B2

Reaction notes

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