2-Fluoroaniline → 3-chloro-N-(2-fluorophenyl)propanamide

HRID 1521670Notes

Reaction equation

HRID 1521670 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:9][CH2:10][CH2:11][C:12](Cl)=[O:13]>O1CCCC1.N1C=CC=CC=1.O>[Cl:9][CH2:10][CH2:11][C:12]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[F:1])=[O:13]

Participants

6

Reactant 2

HCID 95842-FluoroanilineHCID 693643-Chloropropionyl chloride

Product 1

HCID 42560293-chloro-N-(2-fluorophenyl)propanamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-fluoroaniline (20.00 g, 180.0 mmol) in tetrahydrofurane (100 mL) and pyridine (22 mL) was stirred for 15 min, and then 3-chloropropionyl chloride (25.14 g, 198 mmol) in tetrahydrofurane (50 ml) was added at 0° C. The mixture was stirred for 18 h at room temperature under inert atmosphere. After completion of the reaction, the mixture was diluted with water. The aqueous layer was separated and extracted with diethylether. The collected organic parts were washed with water and brine, then dried over Na2SO4, filtered and concentrated under vacuum to afford the title compound (white solid). This intermediate was used directly in the next step without further purification and characterization.

Workup

  1. customAfter completion of the reaction
  2. customThe aqueous layer was separated
  3. extractionextracted with diethylether
  4. washThe collected organic parts were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c7b1e0deeb154d20bd775617967711c0
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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