Dichloromethane → 4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]-2-methylphenol

HRID 2181837Notes

Reaction equation

HRID 2181837 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)=[C:23]([CH3:29])[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:26]=[CH:25][C:24]([OH:27])=[C:23]([CH3:29])[CH:22]=1)(=[O:20])=[O:19])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 22482394HCID 22482394, compound

Product 1

HCID 100008734-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]-2-methylphenolYield 50%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

The title compound was prepared from 6-ethyl-8-fluoro-5-[(4-methoxy-3-methylphenyl)sulfonyl]-5,6-dihydrophenanthridine (0.53 g, 1.3 mmol), tetrabutylammonium iodide (1.2 g, 3.2 mmol), and 1 M boron trichloride in dichloromethane (8.9 mL, 8.9 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 1:1 gradient), followed by re-crystallization from a mixture of dichloromethane-hexane to yield 4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]-2-methylphenol as a homogeneous solid (0.25 g, 50%), m.p. 181° 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 1:1 gradient)
  3. customfollowed by re-crystallization from a mixture of dichloromethane-hexane

Sources & evidence

ORD record
ord-7507716b22c245998a7cefe0f1b35f2d
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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