Isopropyl iodide → 1-Bromo-3-(isopropylsulfanyl)benzene

HRID 1443373

Reaction equation

HRID 1443373 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].I[CH:16]([CH3:18])[CH3:17]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][CH:16]([CH3:18])[CH3:17])[CH:3]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 80597m-Bromobenzenethiol

Product 1

HCID 179787721-Bromo-3-(isopropylsulfanyl)benzeneYield 93.17%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Bromobenzenethiol (1 g, 5.3 mmol) was added to acetone (25 mL). Next was added potassium carbonate (1.46 g, 10.58 mmol) and 2-iodopropane (1.17 g, 6.88 mmol). This was refluxed for 5 h. Reaction was then cooled to rt and filtered through a pad of Celite. The organic was then concentrated in vacuo and taken up in ether at which time a white precipitate crashed out. The organic was then re-filtered through the same celite plug and concentrated in vacuo to provide 1.14 g (93.17%) of 1-bromo-3-isopropylsulfanyl-benzene as an oil. 1H-NMR (methylene chloride -d2) δ 7.54 (s, 1H), 7.37-7.31 (m, 2H), 7.18 (t, J=7.9 Hz, 1H), 3.50-3.36 (m, 1H), 1.31 (d, J=6.1 Hz, 6H); LC-MS RT: 4.15, [M+H]+: 233.2.

Workup

  1. temperatureThis was refluxed for 5 h
  2. customReaction
  3. filtrationfiltered through a pad of Celite
  4. concentrationThe organic was then concentrated in vacuo
  5. filtrationThe organic was then re-filtered through the same celite plug
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b4e48a159e714e78a82320ee483dae08
Source dataset
uspto-grants-2010_02
Patent number
US07659412B2

Linked notes

Loading…