2-Fluoroaniline → N-(2-fluorophenyl)acrylamide

HRID 1020376Notes

Reaction equation

HRID 1020376 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].OP([O-])([O-])=O.[Na+].[Na+].[F:13][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH2:16]>C(Cl)Cl>[F:13][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH:16][C:1](=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 95842-FluoroanilineHCID 13140Acryloyl chlorideHCID 24203Sodium Phosphate, Dibasic

Product 1

HCID 3677416N-(2-fluorophenyl)acrylamideYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of acryloyl chloride (0.70 mL, 8.63 mmol) and sodium phosphate dibasic (2.45 g, 17.26 mmol) in anhydrous methylene chloride (18.0 mL) at 0° C. was added dropwise 2-fluoroaniline (0.834 mL, 8.63 mmol). The reaction mixture was stirred at room temperature for 12 h. It was then filtered over a celite pad, washed with methylene chloride (50 mL) and concentrated to afford N-(2-fluorophenyl)acrylamide (C-4) as a white solid (0.959 g, 68% yield). MS (M+1): m/e 166. This material was used for the next step with no additional purification.

Workup

  1. filtrationIt was then filtered over a celite pad
  2. washwashed with methylene chloride (50 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d01ba857e928488fa0f23f37af1e3344
Source dataset
uspto-grants-2014_05
Patent number
US08716312B2

Reaction notes

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