Dichloromethane → 4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]phenol

HRID 2181835Notes

Reaction equation

HRID 2181835 reaction equation
[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH3:2].B(Cl)(Cl)Cl.ClCCl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:18]([C:21]1[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=1)(=[O:20])=[O:19])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 224823306-Ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine

Product 1

HCID 104300394-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]phenolYield 94%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

The title compound was prepared from 6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine (0.51 g, 1.3 mmol), tetrabutylammonium iodide (1.2 g, 3.2 mmol), and 1 M boron trichloride in dichloromethane (9.0 mL, 9.0 mmol) according to the procedure and in the same manner as described in Example 35, Step b. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:9 to 2:3 gradient), followed by re-crystallization from a mixture of dichloromethane-hexane, to yield 4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]phenol as a solid (0.36 g, 94%), m.p. 151° C.;

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:9 to 2:3 gradient)
  3. customfollowed by re-crystallization from a mixture of dichloromethane-hexane

Sources & evidence

ORD record
ord-877d7ea711f94528a1491dd9881dc3cd
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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