Dichloromethane → HCID 10083945, compound

HRID 1989849Notes

Reaction equation

HRID 1989849 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][C:18]2[C:17]3[C:8](=[C:9]4[C:14](=[CH:15][CH:16]=3)[CH:13]=[C:12]([O:21]C)[CH:11]=[CH:10]4)[CH:7]=[CH:6][C:5]=2[CH:4]=1.C(Cl)Cl.B(Br)(Br)Br>O>[CH:4]1[C:5]2[CH:6]=[CH:7][C:8]3[C:17](=[CH:16][CH:15]=[C:14]4[C:9]=3[CH:10]=[CH:11][C:12]([OH:21])=[CH:13]4)[C:18]=2[CH:19]=[CH:20][C:3]=1[OH:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 86615571HCID 86615571, compound

Product 1

HCID 10083945HCID 10083945, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-60 °C

Procedure

Under an argon gas flow, 24 g (0.083 mol) of 2,8-dimethoxychrysene and 2 L of methylene chloride were charged into a 3 L glass flask equipped with a condenser, and cooled to −60° C. Successively, 4.1 g (0.17 mol) of boron tribromide was slowly dropped into the flask, and then the contents of the flask were stirred at room temperature for 18 h. After completion of the reaction, 1 L of water was added to the flask to separate an organic layer from the reaction solution. The resultant crude crystal was short-passed through silica gel (using THF (tetrahydrofuran) as a developing solvent). The obtained product was concentrated under reduced pressure, and the resultant crude product (25 g) was directly used in the subsequent reaction.

Workup

  1. customequipped with a condenser
  2. additionwas added to the flask
  3. customto separate an organic layer from the reaction solution
  4. concentrationThe obtained product was concentrated under reduced pressure
  5. customthe resultant crude product (25 g) was directly used in the subsequent reaction

Sources & evidence

ORD record
ord-df1e5dd85de44646b7b565f45f41de65
Source dataset
uspto-grants-2010_01
Patent number
US07642380B2

Reaction notes

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