Bromobenzene → HCID 15319859, compound

HRID 2216721Notes

Reaction equation

HRID 2216721 reaction equation
[CH3:1][C:2]1[CH2:6][CH2:5][C:4](=O)[CH:3]=1.[C:8]1([Li])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Li].BrC1C=CC=CC=1.[NH4+].[Cl-]>CCOCC>[CH3:1][C:2]1[CH2:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:3]=1

Participants

7

Reactant 5

HCID 7961BromobenzeneHCID 176913-Methyl-2-cyclopenten-1-oneHCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 178506676HCID 178506676, compound

Product 1

HCID 15319859HCID 15319859, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 25 g (0.26 mol) of 3-methyl-2cyclopenten-1-one in 100 mL of ether was added at −78° C. under argon atmosphere to a solution of phenyl litium in 200 mL of ether, previous prepared from 5.76 g (0.83 mol) of lithium and 44 mL (0.42 mol) of bromobenzene. The reaction mixture was stirred for 4 h and then treated with a 10% aq. solution of NH4Cl. The organic phase was collected, washed with water, dried with MgSO4 and concentrated. The residue was distilled at 54° C./1 mmHg. Yield 24.37 g (60%).

Workup

  1. customThe organic phase was collected
  2. washwashed with water
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated
  5. distillationThe residue was distilled at 54° C./1 mmHg

Sources & evidence

ORD record
ord-aae0809b6627489ba44e19b50070f793
Source dataset
uspto-grants-2006_09
Patent number
US07112638B2

Reaction notes

Loading…