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Cyclohexene → 4-[(8-Fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol

HRID 2181815
Notes
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Reaction equation

HRID 2181815 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].C1CCCCC=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[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:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)(=[O:18])=[O:17])[CH:5]2[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8079CyclohexeneHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 22482267HCID 22482267, compound

Product 1

HCID 103617404-[(8-Fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A stirred suspension of 8-fluoro-5-(4-methoxyphenylsulfonyl)-6-methyl-5,6-dihydrophenanthridine (1.26 g, 3.29 mmol) and cyclohexene (6.0 mL, 59 mmol) was treated drop-wise with a solution of 1 M boron tribromide (20 mL, 20 mmol) in dichloromethane at room temperature under nitrogen. After stirring for 20 hours at room temperature, a saturated, aqueous, sodium bicarbonate solution (300 mL) was added drop-wise, and the resulting mixture extracted with dichloromethane (6×20 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:19 to 1:4 gradient), followed by re-crystallization from a mixture of dichloromethane-hexane to yield the title compound as a homogeneous, white, crystalline, solid (1.1 g, 90%). The melting point, mass spectum, and NMR spectrum of this product were identical to the authentic material prepared in Example 32, Method A, Step e.

Workup

  1. extractionthe resulting mixture extracted with dichloromethane (6×20 mL)
  2. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash column chromatography on silica gel
  6. washeluting with a mixture of ethyl acetate-hexane (1:19 to 1:4 gradient)
  7. customfollowed by re-crystallization from a mixture of dichloromethane-hexane

Sources & evidence

ORD record
ord-84fd628bf95c4f79bc3d0dd668b18cd3
Source dataset
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06894061B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes