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

HRID 2181851Notes

Reaction equation

HRID 2181851 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]=[C:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:7]=[CH:6][C:5]=2[N:4]1[S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33]C)=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH3:2].C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[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]=[C:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:7]=[CH:6][C:5]=2[N:4]1[S:24]([C:27]1[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=1)(=[O:26])=[O:25])[CH3:2]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 22482337HCID 22482337, compound

Product 1

HCID 103669484-[(6-ethyl-8-fluoro-2-phenylphenanthridin-5(6H)-yl)sulfonyl]phenolYield 75.3%

Procedure

A stirred suspension of 6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-2-phenyl-5,6-dihydrophenanthridine (0.13 g, 0.26 mmol) and cyclohexene (0.48 mL, 4.8 mmol) was treated drop-wise at room temperature under nitrogen with a solution of 1 M boron tribromide in dichloromethane (1.6 mL, 1.6 mmol). After stirring for 20 hours at room temperature, the reaction was quenched by the drop-wise addition of a saturated, aqueous, sodium bicarbonate solution (300 mL), followed by extraction with dichloromethane (6×20 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to a crude product. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:4 to 3:7 gradient), followed by re-crystallization from a mixture of ethyl acetate-hexane, to yield 4-[(6-ethyl-8-fluoro-2-phenylphenanthridin-5(6H)-yl)sulfonyl]phenol as a homogeneous solid (0.09 g, 71%), m.p. 207° C.;

Workup

  1. customthe reaction was quenched by the drop-wise addition of a saturated, aqueous, sodium bicarbonate solution (300 mL)
  2. extractionfollowed by extraction with dichloromethane (6×20 mL)
  3. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a crude product
  6. customThe crude product was purified by flash column chromatography on silica gel
  7. washeluting with a mixture of ethyl acetate-hexane (1:4 to 3:7 gradient)
  8. customfollowed by re-crystallization from a mixture of ethyl acetate-hexane

Sources & evidence

ORD record
ord-a42a436e8f15416bb014e2877e0f99b9
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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