Boron Trichloride → HCID 820269, compound

HRID 612598Notes

Reaction equation

HRID 612598 reaction equation
[CH:1]([O:4][C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:18]C)[C:10](=[O:20])[C:9]=2[CH:8]=[CH:7][CH:6]=1)(C)C.B(Cl)(Cl)Cl>C(Cl)Cl>[OH:18][C:15]1[C:16]2[C:17]3[C:9](=[CH:8][CH:7]=[CH:6][C:5]=3[O:4][CH3:1])[C:10](=[O:20])[C:11]=2[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 19594770HCID 19594770, compound

Product 1

HCID 820269HCID 820269, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Prepare a solution of 4-isopropoxy-5-methoxy-fluoren-9-one (0.78 g, 2.9 mmole) in methylene chloride (15 mL) and stir at 0° C. under an argon atmosphere. Dropwise add 9 mL (9.0 mmole) of boron trichloride (1.0 M in methylene chloride and stir the mixture for 1 hour, observing the color change to dark. Quench the reaction with 20 mL water, observing a mild exothermic reaction and an orange precipitate. Filter and wash the solid twice with 100 mL methylene chloride. Separate the organic layer from the filtrate and wash with brine. Dry over magnesium sulfate, filter and remove the solvent. Recrystalize the solid from chloroform/hexane (20:80; Rf =0.2) to give the title compound. Yield; 0.55 g, 84%.

Workup

  1. customQuench
  2. customthe reaction with 20 mL water
  3. customa mild exothermic reaction
  4. filtrationFilter
  5. washwash the solid twice with 100 mL methylene chloride
  6. customSeparate the organic layer from the filtrate
  7. washwash with brine
  8. dry with materialDry over magnesium sulfate
  9. filtrationfilter
  10. customremove the solvent
  11. customRecrystalize the solid from chloroform/hexane (20:80; Rf =0.2)

Sources & evidence

ORD record
ord-26c71f1f22984d2d84e2ddca1701c0e7
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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