N-bromobutanimide → 2-(2-Bromothiophen-3-yl)ethan-1-ol

HRID 1651643Notes

Reaction equation

HRID 1651643 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][OH:8])=[CH:2]1.[Br:9]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:9][C:2]1[S:1][CH:5]=[CH:4][C:3]=1[CH2:6][CH2:7][OH:8]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 83731Thiophene-3-ethanol

Product 1

HCID 193595722-(2-Bromothiophen-3-yl)ethan-1-olYield 99.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 2-(3-thienyl)ethanol (25.0 g, 0.195 mol) in carbon tetrachloride (250 ml) was added N-bromosuccinimide (34.7 g, 0.195 mol) in several portions over a 15 minute period. The mixture was stirred at room temperature for one hour. The succinimide was removed by filtration and the filtrate was concentrated in vacuo at room temperature to give the product as a viscous amber oil (40.2 g) (99%). TLC indicated that the product was pure and mass spectral analysis showed a molecular ion at M/Z 206. NMR supported the structure.

Workup

  1. customThe succinimide was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo at room temperature

Sources & evidence

ORD record
ord-05da1af5a8bd4188b994e3da1f921a0e
Source dataset
uspto-grants-1990_05
Patent number
US04929637

Reaction notes

Loading…