Boron trifluoride etherate → 5-Bromo-2-chloro-3-(4-methoxybenzyl)thiophene

HRID 1469174Notes

Reaction equation

HRID 1469174 reaction equation
[Br:1][C:2]1[S:6][C:5]([Cl:7])=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=O)[CH:3]=1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CC#N>[Br:1][C:2]1[S:6][C:5]([Cl:7])=[C:4]([CH2:8][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 66692728(5-Bromo-2-chlorothiophen-3-yl)(4-methoxyphenyl)methanone

Product 1

HCID 666954545-Bromo-2-chloro-3-(4-methoxybenzyl)thiopheneYield 82%

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

To a solution of methanone 2 (2.68 g, 8.08 mmol) in CH2Cl2/CH3CN (20 mL/20 mL) were added triethylsilane (3.9 mL, 24.2 mmol) and boron trifluoride diethyl etherate (3.1 mL, 24.2 mmol) at 0° C. The mixture was warmed up to room temperature slowly and stirred at room temperature for 15 hours. To the mixture was added aq. saturated K2CO3 solution (50 mL) slowly and extracted with EtOAc (50 mL×2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica column chromatography (Biotage) to provide the desired product 3 (2.09 g, 82%).

Workup

  1. extractionextracted with EtOAc (50 mL×2)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica column chromatography (Biotage)

Sources & evidence

ORD record
ord-b09cc84ade394b96bf97c174a4fab68e
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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