Boron Trichloride → HCID 14188394, compound

HRID 612603Notes

Reaction equation

HRID 612603 reaction equation
C([O:4][C:5]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:6]=1[C:7]1[C:8]([O:21][CH3:22])=[CH:9][C:10]([O:19][CH3:20])=[CH:11][C:12]=1[C:13]2=[O:18])(C)C.B(Cl)(Cl)Cl>C(Cl)Cl>[CH3:20][O:19][C:10]1[CH:9]=[C:8]([O:21][CH3:22])[C:7]2[C:6]3[C:14](=[CH:15][CH:16]=[CH:17][C:5]=3[OH:4])[C:13](=[O:18])[C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 19594890HCID 19594890, compound

Product 1

HCID 14188394HCID 14188394, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Prepare a solution of 5-isopropoxy-2,4-dimethoxy-fluoren-9-one (0.48 g, 1.6 mmole) in 25 mL CH2Cl2 and stir at 0° C. under argon. Dropwise, add boron trichloride (1.0 M in 1.8 mL CH2Cl2, 1.8 mmole) and stir the reaction for 1 hour. Quench with 20 mL water and stir vigorously. Filter and wash twice the resulting precipitate with 100 mL methylene chloride. Separate the organic layer from the filtrate and wash with brine. Dry with MgSO4, filter and strip off the solvent. Recrystallize the solid from CH2Cl2 /hexane (4:6) to obtain the title compound (0.28 g, 1.1 mmole, 69%). Rf =0.3.

Workup

  1. stirringstir
  2. customthe reaction for 1 hour
  3. customQuench with 20 mL water
  4. stirringstir vigorously
  5. filtrationFilter
  6. washwash twice the resulting precipitate with 100 mL methylene chloride
  7. customSeparate the organic layer from the filtrate
  8. washwash with brine
  9. dry with materialDry with MgSO4
  10. filtrationfilter
  11. customRecrystallize the solid from CH2Cl2 /hexane (4:6)

Sources & evidence

ORD record
ord-8676933ae4144598b7ca53c5abe1d437
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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