Hydrochloric Acid → 1-(4-Acetyl-2-fluorophenyl)ethan-1-one

HRID 48382

반응식

HRID 48382 반응식
Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][C:3]=1[F:9].C([O:12][C:13]([Sn])=[CH2:14])C.Cl.C1C[O:20][CH2:19][CH2:18]1>>[C:19]([C:5]1[CH:6]=[CH:7][C:2]([C:13](=[O:12])[CH3:14])=[C:3]([F:9])[CH:4]=1)(=[O:20])[CH3:18]

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 1370041,4-Dibromo-2-fluorobenzeneHCID 57440505HCID 57440505, 화합물

생성물 1

HCID 227432121-(4-Acetyl-2-fluorophenyl)ethan-1-one수율 100%

실험 절차

Into a 100 mL single neck flask were placed 1,4-dibromo-2-fluorobenzene (2.35 g, 9.2 mmol), dichlorobis(triphenylphosphine) palladium (II) (0.645 g, 0.92 mmol), tributyt (1-ethoxyvinyl)tin (10 g, 27.7 mmol), in THF (50 mL), and the mixture was heated at reflux while stirring for 18 hours. The reaction was cooled to room temperature and poured into 5N HCl (20 mL). The product was extracted with EtOAc and the organic layer was separated and washed twice with water, dried over anhydrous Na2SO4, filtered, and concentrated under reduced vacuum. The resulting semi-solid was purified via flash chromatography (Silica gel, isocratic) and eluting with a solvent of Hexanes/EtOAc 90:10 to provide the intermediate title compound, 1-(4-acetyl-2-fluorophenyl)ethan-1-one, (1.65 g, 100%) as a solid. Electron spray M.S. 180.9 (M*)

후처리

  1. customInto a 100 mL single neck flask were placed
  2. temperatureat reflux
  3. extractionThe product was extracted with EtOAc
  4. customthe organic layer was separated
  5. washwashed twice with water
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced vacuum
  9. customThe resulting semi-solid was purified via flash chromatography (Silica gel, isocratic)
  10. washeluting with a solvent of Hexanes/EtOAc 90:10

출처 및 근거

ORD 기록
ord-4641edbb623f42159330a1ff7bd59c50
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703425B2

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