Ethylene Oxide → 2-(4-bromothiophen-2-yl)ethanol

HRID 2371023Notes

Reaction equation

HRID 2371023 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([Br:7])[CH:6]=1.[Li]CCCC.[O:13]1[CH2:15][CH2:14]1>CCOCC>[Br:7][C:5]1[CH:6]=[C:2]([CH2:15][CH2:14][OH:13])[S:3][CH:4]=1

Participants

5

Reactant 3

HCID 6354Ethylene OxideHCID 2724560Thiophene, 2,4-dibromo-HCID 178418339Butyllithium

Product 1

HCID 639686112-(4-bromothiophen-2-yl)ethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2,4-dibromothiophene (1 g, 4.13 mmol) in anhydrous ether was added n-BuLi (1.66 mL, 4.13 mmol) at −78° C. dropwise. After stirring at −78° C. for 0.5 hr, oxirane (0.32 mL, 19.28 mmol/mL in ether) was added to the reaction mixture quickly. After stirring at 0° C. for 1.5 hr, the reaction mixture was quenched with aqueous NH4Cl solution, extracted with EtOAc, concentrated and purified to give the desired product.

Workup

  1. stirringAfter stirring at 0° C. for 1.5 hr
  2. customthe reaction mixture was quenched with aqueous NH4Cl solution
  3. extractionextracted with EtOAc
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-88d86e4da1f04ab7a9afef193f30499a
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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