Acetic Anhydride → N-(3-Chloro-4-fluorophenyl)acetamide

HRID 1004571Notes

Reaction equation

HRID 1004571 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].[C:10](OC(=O)C)(=[O:12])[CH3:11]>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][C:8]=1[F:9]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 97083-Chloro-4-fluoroaniline

Product 1

HCID 589188N-(3-Chloro-4-fluorophenyl)acetamideYield 98%

Procedure

Acetic anhydride (30 mL) was added at room temperature dropwise to 3-chloro-4-fluoroaniline (13.0 g, 0.1 mol) and stirred for 3 h. The reaction mixture was poured on ice (300 g) and the solid was filtered and dried to afford N-(3-chloro-4-fluorophenyl)acetamide (18.4 g, 98%) as a white solid. mp 96-97° C.; IR (KBr) 3303, 1671 cm-1 ; 1H NMR (CDCl3) δ 2.20 (s, 3H, CH3), 7.05 (t, J=8.9 Hz, 1H), 7.28 (m,1H), 7.66 (d, J=4.6 Hz, 1H), 8.05 (s, 1H, NH); Mass (m/z) 187 (M+).

Workup

  1. additionThe reaction mixture was poured on ice (300 g)
  2. filtrationthe solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-dac223a43499495a96d9c4b23dbb7830
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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