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

HRID 2181849Notes

Reaction equation

HRID 2181849 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]([Cl:29])[CH:22]=1)(=[O:20])=[O:19])[CH3:2].B(Cl)(Cl)Cl.ClCCl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:29][C:23]1[CH:22]=[C:21]([S:18]([N:4]2[CH:3]([CH2:1][CH3:2])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=3)[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=3)(=[O:19])=[O:20])[CH:26]=[CH:25][C:24]=1[OH:27]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 22482342HCID 22482342, compound

Product 1

HCID 99793892-chloro-4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]phenolYield 41%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

The title compound was prepared from 6-ethyl-8-fluoro-5-[(3-chloro-4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine (0.41 g, 0.96 mmol), tetrabutylammonium iodide (0.85 g, 2.3 mmol), and 1 M boron trichloride in dichloromethane (6.7 mL, 6.7 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 (20:80 to 35:65 gradient), followed by re-crystallization from a mixture of ethyl acetate-hexane, to yield 2-chloro-4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]phenol as a homogeneous solid (0.16 g, 41%), m.p. 174-177° C.;

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (20:80 to 35:65 gradient)
  3. customfollowed by re-crystallization from a mixture of ethyl acetate-hexane

Sources & evidence

ORD record
ord-7085b43db0144f709e81e423c66ba17a
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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