2-Bromothiophene → HCID 58495549, compound

HRID 1191107Notes

Reaction equation

HRID 1191107 reaction equation
[Br:1][C:2]1[S:6][CH:5]=[CH:4][CH:3]=1.[CH3:7][C:8]([CH3:14])([CH3:13])[CH2:9][C:10](Cl)=[O:11].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[N+](C)([O-])=O>[Br:1][C:2]1[S:6][C:5]([C:10](=[O:11])[CH2:9][C:8]([CH3:14])([CH3:13])[CH3:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 138512-BromothiopheneHCID 815143,3-Dimethylbutanoyl chlorideHCID 2733225Ytterbium triflate

Product 1

HCID 58495549HCID 58495549, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

Stir overnight at room temperature a mixture of 5-bromothiophene (1 g, 6.1 mmol), 3,3-dimethylbutyryl chloride (1.3 mL, 9.1 mmol) and ytterbium(III) trifluoromethanesulfonate (378 mg, 0.6 mmol) in nitromethane (15 mL). Wash the mixture sequentially with water, saturated aqueous NaHCO3 and water. Extract with chloroform, dry over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane to obtain the desired intermediate (1.3 g, 80%).

Workup

  1. washWash the mixture sequentially with water, saturated aqueous NaHCO3 and water
  2. extractionExtract with chloroform
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the crude mixture by chromatography on silica gel eluting with hexane

Sources & evidence

ORD record
ord-144c0660d4f047f3b0529e43891eaf29
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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