Dichloromethane → 2-fluoro-4-[(8-fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol

HRID 2181856Notes

Reaction equation

HRID 2181856 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[C:21]([F:27])[CH:20]=1)(=[O:18])=[O:17])[CH:5]2[CH3:28].C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[F:27][C:21]1[CH:20]=[C:19]([S:16]([N:6]2[CH:5]([CH3:28])[C:4]3[C:13](=[CH:14][CH:15]=[C:2]([F:1])[CH:3]=3)[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]2=3)(=[O:17])=[O:18])[CH:24]=[CH:23][C:22]=1[OH:25]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 224822898-Fluoro-5-[(3-fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Product 1

HCID 103401602-fluoro-4-[(8-fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenolYield 82%

Procedure

The title compound was prepared from 8-fluoro-5-[(3-fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.50 g, 1.3 mmol), cyclohexene (2.3 mL, 22 mmol), and 1 M boron tribromide in dichloromethane (7.5 mL, 7.5 mmol) according to the procedure and in the same manner as described in Example 47, Step b. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:4), followed by trituration from hexane, to yield 2-fluoro-4-[(8-fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol as a homogeneous solid (0.40 g, 82%), m.p. 191° C.;

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:4)

Sources & evidence

ORD record
ord-de0dd35684734f8ba9c093389222e50f
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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