Acetone → 2-(3,5-Dibromothiophen-2-yl)propan-2-ol

HRID 1859537

Reaction equation

HRID 1859537 reaction equation
Br[C:2]1[S:3][C:4]([Br:8])=[CH:5][C:6]=1[Br:7].CCCCCC.[Li]CCCC.[CH3:20][C:21]([CH3:23])=[O:22]>CCOCC>[Br:7][C:6]1[CH:5]=[C:4]([Br:8])[S:3][C:2]=1[C:21]([OH:22])([CH3:23])[CH3:20]

Participants

6

Reactant 4

HCID 180AcetoneHCID 8058HexaneHCID 76592Thiophene, 2,3,5-tribromo-HCID 178418339Butyllithium

Product 1

HCID 225727272-(3,5-Dibromothiophen-2-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2,3,5-tribromothiophene (8.17 g, 25 mmol) in Et2O (N2 atmosphere) was cooled to −78° C. and treated with a 1.6 M hexane solution of nBuLi (15.6 mL, 25 mmol). The mixture was then stirred for 10 minutes, then treated with acetone (1.84 mL, 25 mmol). The mixture was then stirred for 30 minutes and quenched with H2O. The mixture was extracted with Et2O; the organic layers were combined, dried (MgSO4), and the solvent removed in vacuo. The residue was filtered through a plug of silica gel (gradient elution from hexanes to EtOAc) to provide the title compound.

Workup

  1. stirringThe mixture was then stirred for 30 minutes
  2. customquenched with H2O
  3. extractionThe mixture was extracted with Et2O
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. filtrationThe residue was filtered through a plug of silica gel (gradient elution from hexanes to EtOAc)

Sources & evidence

ORD record
ord-9efd2e7c19d04d248fc0530be543a158
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Linked notes

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