Acetic Anhydride → 4'-Chloro-2'-fluoroacetanilide

HRID 1430446Notes

Reaction equation

HRID 1430446 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[C:10](OC(=O)C)(=[O:12])[CH3:11]>C(O)(=O)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:10](=[O:12])[CH3:11])=[C:4]([F:9])[CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 938984-Chloro-2-fluoroaniline

Product 1

HCID 8531744'-Chloro-2'-fluoroacetanilideYield 95.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-chloro-2-fluoroaniline (5.0 g, 34.3 mmol) in acetic acid (3 mL) was treated with acetic anhydride (6.45 mL, 68.7 mmol) and stirred at RT for 2 h. The mixture was poured onto ice water, stirred for 2 h and the resulting solid collected via filtration and dried to afford N-(4-chloro-2-fluorophenyl)acetamide (6.12 g, 95% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.80 (s, 1H), 7.91 (t, J=8.7 Hz, 1H), 7.45 (dd, J=10.8, 2.4 Hz, 1H), 7.22 (d, J=8.9 Hz, 1H), 2.07 (s, 3H).

Workup

  1. additionThe mixture was poured onto ice water
  2. stirringstirred for 2 h
  3. filtrationthe resulting solid collected via filtration
  4. customdried

Sources & evidence

ORD record
ord-76fb67da8a7d43f0ac386011f35e1253
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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