Hydrochloric Acid → 2,7-Dichloro-9-methylfluorene

HRID 2259279Notes

Reaction equation

HRID 2259279 reaction equation
[CH3:1][CH:2]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[Cl:15]N1C(=O)CCC1=O.[ClH:23]>C(#N)C>[Cl:23][C:5]1[CH:6]=[CH:7][C:8]2[C:9]3[C:14](=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=3)[CH:2]([CH3:1])[C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 172999-MethylfluoreneHCID 31398Chlorosuccinimide

Product 1

HCID 143941082,7-Dichloro-9-methylfluoreneYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

9-Methylfluorene (43.6 g, 0.24 mol) and N-chlorosuccinimide (64.5 g, 0.48 mol) were suspended in 25 mL of acetonitrile and cooled in an ice-water bath. Then 20 mL of concentrated HCl was added dropwise and the solution was stirred at room temperature overnight. The precipitate was filtered and dried. Recrystallization from EtOH and water gave 24 g (41%) of 2,7-dichloro-9-methylfluorene as white crystals, mp 110°-112° C. FT IR: 3425, 1450, 1407, 1273, 1167, 1070, 851,818 cm-1 ; H1NMR (CDCl3, 300 MHz) δ 7.3-7.8 (m, 6H, 3.9-4.1 (q, 1H), 1.2-1.3 (d, 2H).

Workup

  1. temperaturecooled in an ice-water bath
  2. filtrationThe precipitate was filtered
  3. customdried
  4. customRecrystallization from EtOH and water

Sources & evidence

ORD record
ord-976ed97be98b493090f66911d803d984
Source dataset
uspto-grants-1995_12
Patent number
US05472973

Reaction notes

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