4-Fluoroaniline → HCID 10377289, compound

HRID 1428940Notes

Reaction equation

HRID 1428940 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH:9]1[C:14]([C:15]([CH2:17]Br)=[O:16])=[CH:13][CH:12]=[C:11]([F:19])[CH:10]=1>C1COCC1>[F:19][C:11]1[CH:12]=[CH:13][C:14]([C:15](=[O:16])[CH2:17][NH:6][C:5]2[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-one

Product 1

HCID 10377289HCID 10377289, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

1.3 mL 4-fluoroaniline was added to 1 g 2-bromo-4-fluoroacetophenone in 20 mL THF. The reaction was stirred 3 h at RT and 4 h at 40° C. The mixture was filtered and the filtrate diluted with ethyl acetate and extracted with water. The organic layer was dried and evaporated. Diisopropylether was added to the residue. The precipitate was filtered and dried to yield 0.42 g desired product. Rt: 1.53 min (method B), (M+H)+: 248

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate diluted with ethyl acetate
  3. extractionextracted with water
  4. customThe organic layer was dried
  5. customevaporated
  6. additionDiisopropylether was added to the residue
  7. filtrationThe precipitate was filtered
  8. customdried

Sources & evidence

ORD record
ord-6f2733643ed2478c9ae7d85ee37980ea
Source dataset
uspto-grants-2015_01
Patent number
US08937176B2

Reaction notes

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