Dichloromethane → 2-Acetyl-7-cyanofluorene

HRID 1077303

Reaction equation

HRID 1077303 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][C:10](Br)=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].ClCCl.[N:21]1C2C(=CC=CC=2)C=C[CH:22]=1>>[C:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][C:10]([C:22]#[N:21])=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 7047QuinolineHCID 2706752-Acetyl-7-bromofluorene

Product 1

HCID 215039022-Acetyl-7-cyanofluorene

Procedure

A mixture of 2-acetyl-7-bromofluorene (13.2 g.) and cuprous cyanide (8.2 g.) in quinoline (40 ml.) was heated to reflux for 40 minutes, cooled to 100° and poured into a mixture of ice-cold dilute aqueous ammonia and dichloromethane. The organic layer was separated, filered to remove a yellow solid, washed with N-hydrochloric acid, dried over sodium sulphate and evaporated. The residual solid was recrystallised from ethanol containing a small amount of dimethylformamide to give 2-acetyl-7-cyanofluorene m.p. 182°-186° .

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 40 minutes
  3. temperaturecooled to 100°
  4. customThe organic layer was separated
  5. customto remove a yellow solid
  6. washwashed with N-hydrochloric acid
  7. dry with materialdried over sodium sulphate
  8. customevaporated
  9. customThe residual solid was recrystallised from ethanol containing a small amount of dimethylformamide

Sources & evidence

ORD record
ord-feb3d53db7234171a20b91fe1ce3c7a7
Source dataset
uspto-grants-1976_05
Patent number
US03959482

Linked notes

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