Chloroacetyl chloride → Fluorenone

HRID 651226Notes

Reaction equation

HRID 651226 reaction equation
C(=O)(O)[O-].[Na+].N[C:7]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:20])[C:9]=2[CH:8]=1.ClCC(Cl)=O>C(OCC)(=O)C>[CH:12]1[C:11]2[C:10](=[O:20])[C:9]3[C:17](=[CH:18][CH:19]=[CH:7][CH:8]=3)[C:16]=2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 183572-AminofluorenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 10241FluorenoneYield 105.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A saturated solution of sodium bicarbonate (5 mL) was added to a solution of 2-amino-9-fluorenone (190 mg. 0.97 mmol) in ethyl acetate (5 mL). Next, chloroacetyl chloride (0.4 mL, 4.8 mmol) was added, and the reaction mixture was stirred at room temperature for 1 hour. The ethyl acetate layer was separated, and washed thoroughly with cold water. It was then dried under vacuum to give 2-N-chloroacetyl)-9-fluorenone (185 mg, 70%).

Workup

  1. customThe ethyl acetate layer was separated
  2. washwashed thoroughly with cold water
  3. customIt was then dried under vacuum

Sources & evidence

ORD record
ord-c3b6b8dc6f744a6ea35c3a8737624b4c
Source dataset
uspto-grants-2001_08
Patent number
US06277990B1

Reaction notes

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