Cyclohexene → HCID 10072135, compound

HRID 2181809Notes

Reaction equation

HRID 2181809 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[N:12]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:11]([CH2:27][CH3:28])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]=2[CH:3]=1.C1CCCCC=1.B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[N:12]([S:16]([C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)(=[O:18])=[O:17])[CH:11]([CH2:27][CH3:28])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8079CyclohexeneHCID 25134Boron tribromideHCID 22482331HCID 22482331, compound

Product 1

HCID 10072135HCID 10072135, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred and cooled solution of 2-bromo-6-ethyl-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine (1.13 g, 2.46 mmol) and cyclohexene (2.5 mL, 24.6 mmol) in dichloromethane (5 mL) was treated drop-wise under nitrogen at −30° C. with boron tribromide (2.5 mL, 24.6 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 to yield the title compound as a gray powder (0.982 g, 2.21 mmol, 90%), which was confirmed by LCMS (ES−, FA, CV=20 or 5).

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

Sources & evidence

ORD record
ord-88c73d7bf3814f74957cd748c71ecec4
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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