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

HRID 1521627Notes

Reaction equation

HRID 1521627 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]>ClCCl.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

5

Reactant 2

HCID 95842-FluoroanilineHCID 693643-Chloropropionyl chloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-fluoroaniline (15 g, 0.135 mol) in dichloromethane (100 mL) was added 3-chloropropanoyl chloride (15.168 mL, 0.135 mol) under cooling condition (0° C.) with constant stirring. Reaction mass was allowed to stir at room temperature for 2 h. The reaction mixture was diluted with water (200 mL) and extracted with dichloromethane (4×100 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to obtain the title compound. MS (M+1): 201.9.

Workup

  1. customReaction mass
  2. extractionextracted with dichloromethane (4×100 mL)
  3. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-75cc37c47a5b499aa228834ce0bdd350
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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