2-Bromothiophene → HCID 67257977, compound

HRID 2371018Notes

Reaction equation

HRID 2371018 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[CH2:7]([O:9][CH:10](OCC)[CH2:11][NH2:12])[CH3:8].C(S(O)(=O)=O)(F)(F)F.[OH-].[K+]>O1CCOCC1>[Br:1][C:2]1[S:3][CH:4]=[C:5]2[C:6]=1[CH2:8][CH2:7][O:9][CH:10]2[CH2:11][NH2:12]

Participants

6

Reactant 4

HCID 138512-BromothiopheneHCID 14797Potassium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 695242,2-Diethoxyethylamine

Product 1

HCID 67257977HCID 67257977, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
22 °C

Procedure

Bromothiophene (0.31 g, 1.5 mmol) and aminoacetaldehyde diethyl acetal (0.3 g, 2.25 mmol) were combined with 1,4-dioxane (2 mL). CF3SO3H (0.45 g, 3.0 mmol) was added and the reaction mixture was stirred at 22° C. for 2 hr at which time the mixture was made basic with 10% KOH (aq.) and the aqueous layer was extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent removed in vacuo to afford the crude amine product.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc (3×50 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-9440c394bb94409cb72d290fa2d92790
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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