Thiophenol → 1-(3,6-dibromo-9H-carbazol-9-yl)-3-(phenylthio)propan-2-ol

HRID 62173Notes

Reaction equation

HRID 62173 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([CH2:23][CH:24]3[CH2:26][O:25]3)[C:14]3[C:19]([C:20]=2[CH:21]=1)=[CH:18][C:17]([Br:22])=[CH:16][CH:15]=3>CO>[Br:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([CH2:23][CH:24]([OH:25])[CH2:26][S:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:14]3[C:19]([C:20]=2[CH:21]=1)=[CH:18][C:17]([Br:22])=[CH:16][CH:15]=3

Participants

4

Reactant 2

HCID 7969ThiophenolHCID 27754733,6-dibromo-9-((oxiran-2-yl)methyl)-9H-carbazole

Product 1

HCID 468532991-(3,6-dibromo-9H-carbazol-9-yl)-3-(phenylthio)propan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Benzenethiol (30 Tl, 0.29 mmol) was added to a solution of 3,6-dibromo-9-(oxiran-2-ylmethyl)-9H-carbazole (epoxide 2-A, 101.6 mg, 0.27 mmol) in 5.0 ml MeOH at r.t. The reaction mixture was heated to 80° C. and stirred overnight at the same temperature. The reaction was monitored by lc/ms for the consumption of SM. The reaction was cooled, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over Na2SO4, filtered and condensed.

Workup

  1. customlc/ms for the consumption of SM
  2. temperatureThe reaction was cooled
  3. additiondiluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customcondensed

Sources & evidence

ORD record
ord-5c52c6334595429691da345b10b25a6c
Source dataset
uspto-grants-2016_09
Patent number
US09446042B2

Reaction notes

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