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

HRID 2181866Notes

Reaction equation

HRID 2181866 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:10]([N:13]2[CH:26]([CH3:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]2=3)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8]C.C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[F:1][C:2]1[CH:3]=[C:4]([S:10]([N:13]2[CH:26]([CH3:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]2=3)(=[O:11])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 224822965-[(3-Fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Product 1

HCID 224822772-fluoro-4-[(6-methylphenanthridin-5(6H)-yl)sulfonyl]phenolYield 74%

Procedure

The title compound was prepared from 5-[(3-fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.5 g, 1.3 mmol), cyclohexene (0.33 mL, 3.25 mmol) and 1.0 M boron tribromide in dichloromethane (7.8 mL, 7.8 mmol) according to the procedure and in the same manner as described in Example 1, step b. The crude product was purified by flash column chromatography on silica gel, eluting sequentially with dichloromethane and ethyl acetate to yield 2-fluoro-4-[(6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol (0.35 g, 0.96 mmol, 74%) as a light-yellow solid, m.p. 172-174° C.;

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting sequentially with dichloromethane and ethyl acetate

Sources & evidence

ORD record
ord-88b5b185ba99454390bb13a8bfcface9
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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