Cyclohexene → HCID 10344102, compound

HRID 2181810Notes

Reaction equation

HRID 2181810 reaction equation
[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[CH:9]=[C:8]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[CH:18]=3)[CH:7]=[CH:6][C:5]=2[N:4]1[S:25]([C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH3:2].C1CCCCC=1.B(Br)(Br)Br>ClCCl>[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[CH:9]=[C:8]([C:17]3[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=3)[CH:7]=[CH:6][C:5]=2[N:4]1[S:25]([C:28]1[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=1)(=[O:27])=[O:26])[CH3:2]

Participants

5

Reactant 3

HCID 8079CyclohexeneHCID 25134Boron tribromideHCID 10479890HCID 10479890, compound

Product 1

HCID 10344102HCID 10344102, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred and cooled solution of 4-{[6-ethyl-2-(3-methoxyphenyl)phenanthridin-5(6H)-yl]sulfonyl}phenol (0.645 g, 1.36 mmol) and cyclohexene (1.1 mL, 10.9 mmol) in dichloromethane (5 mL) was treated drop-wise under nitrogen at −30° C. with boron tribromide (1.03 mL, 10.9 mmol). After the addition was completed, the reaction mixture was allowed to warm to room temperature and stirred for four hours. The reaction was cooled to −30° C. and quenched with methanol (1 mL). The solvent was removed in vacuo, and the residue was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:3); to yield the title compound (0.473 g, 1.03 mmol, 76%), which was characterized by LCMS (ES+, FA, CV=20 or 5), m.p. 105° C.;

Workup

  1. additionAfter the addition
  2. stirringstirred for four hours
  3. temperatureThe reaction was cooled to −30° C.
  4. customquenched with methanol (1 mL)
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel
  7. washeluting with a mixture of ethyl acetate-hexane (1:3)

Sources & evidence

ORD record
ord-9035e0e2444b4fb8b52790320eac3368
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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