Boron Trichloride → HCID 10879298, compound

HRID 612618Notes

Reaction equation

HRID 612618 reaction equation
[CH3:1][O:2][C:3]1[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][C:13]=3[O:16]C(C)C)[C:8](=[O:20])[C:7]=2[CH:6]=[C:5]([O:21]C(C)C)[CH:4]=1.B(Cl)(Cl)Cl>C(Cl)Cl>[OH:21][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][C:13]=3[OH:16])[C:8](=[O:20])[C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 15118868HCID 15118868, compound

Product 1

HCID 10879298HCID 10879298, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-methoxy-2,5-bis-(1-methylethoxy)-9H-fluoren-9-one (0.58 g, 1.8 mmol) in CH2Cl2 (15.0 mL) is added BCl3 (7.2 mL, 7.2 mmol) (1.0M) at 0° C. The green mixture is allowed to warm to ambient temperature and stirred for 2 hours under argon. The mixture is cooled to OC and quenched with H2O (20 mL). The precipitated red solid is removed by filtration and recrystallized from MeOH/H2O affording 0.331 g (76%) of the title compound as a red solid: mp 235-237° C. (lit., 238-240° C.); IR (KBr) 1697, 1614, 1597 cm-1 ; UV (EtOH) 1 max=265, 274 and 338 nm (e=32,576, 36,000 and 3,406 nm.

Workup

  1. temperatureThe mixture is cooled to OC
  2. customquenched with H2O (20 mL)
  3. customThe precipitated red solid is removed by filtration
  4. customrecrystallized from MeOH/H2O affording 0.331 g (76%) of the title compound as a red solid
  5. custommp 235-237° C. (lit., 238-240° C.)

Sources & evidence

ORD record
ord-7fd33efbd4a24d9b85981cb8d03a3508
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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