Chloroacetyl chloride → HCID 14998428, compound

HRID 539577Notes

Reaction equation

HRID 539577 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].[Cl:10][CH2:11][C:12](Cl)=[O:13].[OH-].[Na+]>ClCCl>[Cl:10][CH2:11][C:12]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9])=[O:13]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 1857632-Amino-5-fluorophenol

Product 1

HCID 14998428HCID 14998428, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-5-fluorophenol (1.0 g, 7.87 mmol) in dichloromethane (50 mL) at 0° C. was added 2-Chloroacetyl chloride (978 mg, 8.66 mmol). The reaction mixture was stirred at rt for 2 h, followed by addition of aqueous saturated NaOH solution. The organic layer was washed with brine, dried over Na2SO4 and solvent was removed under reduced pressure to afford 550 mg (35%) of 2-chloro-N-(4-fluoro-2-hydroxyphenyl)acetamide (I-21) as a brown solid. ESI-LC/MS (m/z): (M−H)− 201.6, RT 2.65 min.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over Na2SO4 and solvent
  3. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-3b048764b87a458dae09e216cf15f14a
Source dataset
uspto-grants-2014_10
Patent number
US08871754B2

Reaction notes

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