3-Chloropropionyl chloride → 3-chloro-N-(2-fluoro-4-hydroxyphenyl)propanamide

HRID 55846

Reaction equation

HRID 55846 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[Cl:10][CH2:11][CH2:12][C:13](Cl)=[O:14]>CC(C)=O>[Cl:10][CH2:11][CH2:12][C:13]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9])=[O:14]

Participants

4

Reactant 2

HCID 693643-Chloropropionyl chlorideHCID 27359194-Amino-3-fluorophenol

Product 1

HCID 669800713-chloro-N-(2-fluoro-4-hydroxyphenyl)propanamideYield 50.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Amino-3-fluorophenol (3.4 g) was mixed with 3-chloropropanoyl chloride (3.56 g) in acetone (60 mL) and heated at reflux over 3 hours. After aqueous work-up with EtOAc/water, the isolated organic layers were dried over Na2SO4 and concentrated in vacuo. The crude product was purified with silica gel chromatography to give the product (2.95 g) as a light brown solid.

Workup

  1. temperatureheated
  2. temperatureat reflux over 3 hours
  3. dry with materialAfter aqueous work-up with EtOAc/water, the isolated organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified with silica gel chromatography

Sources & evidence

ORD record
ord-2e11691e25a74dbe9424770cd4a8d518
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Linked notes

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