Cesium carbonate → 5-Bromo-2-chloro-3-(4-propoxybenzyl)thiophene

HRID 1469176Notes

Reaction equation

HRID 1469176 reaction equation
[Br:1][C:2]1[S:6][C:5]([Cl:7])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:3]=1.I[CH2:17][CH2:18][CH3:19].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[Br:1][C:2]1[S:6][C:5]([Cl:7])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 336431-IodopropaneHCID 666909044-((5-Bromo-2-chlorothiophen-3-yl)methyl)phenol

Product 1

HCID 666936375-Bromo-2-chloro-3-(4-propoxybenzyl)thiopheneYield 105.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of phenol 4 (500 mg, 1.65 mmol) in acetone (25 mL) were added 1-iodopropane (0.5 mL, 4.95 mmol) and Cs2CO3 (460 mg, 4.95 mmol) at room temperature. The mixture was stirred at 60° C. for 12 hours. The reaction mixture was cooled to room temperature and filtered off through celite. The filtrate was concentrated in vacuo. The residue was purified by silica column chromatography (Biotage) to provide the title compound 5 (600 mg, 99%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered off through celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was purified by silica column chromatography (Biotage)

Sources & evidence

ORD record
ord-958801c9981e4be9b26bf2dc402475e9
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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