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

HRID 921966Notes

Reaction equation

HRID 921966 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 the 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 and were then dried over Na2SO4, filtered and concentrated under vacuum to afford the title compound as a white solid. This intermediate was used directly in the next step without further purification and characterization.

Workup

  1. customAfter the 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 materialwere then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-69c6041e9f6c445e88670bdd375e20a8
Source dataset
uspto-grants-2016_03
Patent number
US09278093B2

Reaction notes

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