Tetrahydrofuran → 2-(2-Bromo-4-fluorophenyl)acetamide

HRID 558128Notes

Reaction equation

HRID 558128 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10](Cl)=[O:11].[OH-].[NH4+:14].C1COCC1>C(Cl)(Cl)Cl.CC(O)C>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([NH2:14])=[O:11]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14923Ammonium HydroxideHCID 86640660HCID 86640660, compound

Product 1

HCID 123838282-(2-Bromo-4-fluorophenyl)acetamideYield 2,872.9%

Reagents, catalysts & solvents 1

HCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

Combine (2-bromo-4-fluoro-phenyl)-acetyl chloride (3.5 g, 14 mmol), ammonium hydroxide (8.8 M in water, 50 mL, 0.45 mmol) and THF (10 mL) in a pressure vessel. Seal the vessel and stir the mixture overnight at RT. Dilute the mixture with chloroform-IPA (3:1, 100 mL). Wash the organic phase with aqueous saturated sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to give the title compound as a white solid (3.0 g, 93%). MS (ES) m/z 232/234 [M+1]+.

Workup

  1. customSeal the vessel
  2. washWash the organic phase with aqueous saturated sodium chloride and water
  3. dry with materialDry the mixture over sodium sulfate
  4. concentrationConcentrate the solution in vacuo

Sources & evidence

ORD record
ord-8e2a3ce6113e429d875bd8390dc8c885
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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