Acetic Acid → 2-(5-bromothiophen-2-yl)ethanol

HRID 2371025Notes

Reaction equation

HRID 2371025 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][OH:8].CC(O)=O.C1C(=O)N([Br:20])C(=O)C1.O>C(Cl)(Cl)Cl>[Br:20][C:5]1[S:1][C:2]([CH2:6][CH2:7][OH:8])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 67184N-bromobutanimideHCID 794002-Thiopheneethanol

Product 1

HCID 207506172-(5-bromothiophen-2-yl)ethanol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-(thiophen-2-yl)ethanol (3 g, 23.4 mmol, 1 eq) and HOAc (5 mL) in CHCl3 was added NBS in portions at room temperature. After stirring at room temperature overnight, the reaction mixture was poured into water and extracted with CHCl3 twice. The combined organic layer was dried over Na2SO4, concentrated and purified by column chromatography to give the desired product.

Workup

  1. extractionextracted with CHCl3 twice
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-a6676666007c4a4cb36296d636198a6c
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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