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

HRID 2181846Notes

Reaction equation

HRID 2181846 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)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:5]2[CH3:27].B(Br)(Br)[Br:29].ClCCl>C(=O)(O)[O-].[Na+]>[Br:29][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:5]([CH3:27])[C:4]3[C:13](=[CH:14][CH:15]=[C:2]([F:1])[CH:3]=3)[C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 22482267HCID 22482267, compound

Product 1

HCID 103663764-[(2-Bromo-8-fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

8-Fluoro-5-(4-methoxyphenylsulfonyl)-6-methyl-5,6-dihydrophenanthridine (0.64 g, 1.7 mmol) was treated with 1 M boron tribromide in dichloromethane (6.6 mL, 6.6 mmol) and stirred at room temperature for twelve hours. A solution of saturated, aqueous, sodium bicarbonate (50 mL) was added slowly to the reaction, followed by extraction of the mixture with dichloromethane (6×20 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to a crude material. The crude material was filtered through a short column of silica gel, eluted with a mixture of ethyl acetate-hexane (1:4), and the filtrate concentrated in vacuo to a solid. After trituration with dichloromethane and filtration, the title compound was obtained as a homogeneous solid (0.23 g, 37%), m.p. 237-239° C.;

Workup

  1. extractionfollowed by extraction of the mixture with dichloromethane (6×20 mL)
  2. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to a crude material
  5. filtrationThe crude material was filtered through a short column of silica gel
  6. washeluted with a mixture of ethyl acetate-hexane (1:4)
  7. concentrationthe filtrate concentrated in vacuo to a solid
  8. filtrationAfter trituration with dichloromethane and filtration

Sources & evidence

ORD record
ord-b6630ed8aac0414ea1116206a714c914
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

Loading…