Water → 2-(2-Bromothiophen-3-yl)ethan-1-ol

HRID 2199569Notes

Reaction equation

HRID 2199569 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[S:9]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10]1.C(Cl)Cl.O>CC(O)=O>[Br:8][C:10]1[S:9][CH:13]=[CH:12][C:11]=1[CH2:14][CH2:15][OH:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 83731Thiophene-3-ethanol

Product 1

HCID 193595722-(2-Bromothiophen-3-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

NBS (9.53 g, 53.6 mmol) was added portionwise to a solution of 3-thiopheneethanol 6.87 g, 53.6 mmol) in AcOH (30 ml). The temperature was raised to 40° C. and mixture was stirred for 1 h. DCM (400 ml) and water was added. The organic layer was washed with water and sat. NaHCO3. The organic layer evaporated and residue purified by flash chromatography using 25-33% EtOAc in iso-hexane. Yield: 5.39 g (49%); colourless oil. 1H NMR (400 MHz, CDCl3): δ 2.89 (t, J 6.4 Hz, 2H), 3.85 (t, J 6.4 Hz, 2H), 6.89 (d, J 5.6 Hz, 1H), 7.26 (d, J 5.6 Hz, 1H).

Workup

  1. washThe organic layer was washed with water and sat. NaHCO3
  2. customThe organic layer evaporated
  3. customresidue purified by flash chromatography

Sources & evidence

ORD record
ord-bca4027ca9cd4415877e6996018729a8
Source dataset
uspto-grants-2016_06
Patent number
US09359311B2

Reaction notes

Loading…