N-bromobutanimide → 2-Bromo-3-methoxycyclopent-2-enone

HRID 1053901Notes

Reaction equation

HRID 1053901 reaction equation
[CH3:1][O:2][C:3]1[CH2:7][CH2:6][C:5](=[O:8])[CH:4]=1.[Br:9]N1C(=O)CCC1=O>ClCCl>[Br:9][C:4]1[C:5](=[O:8])[CH2:6][CH2:7][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 6434763-Methoxycyclopent-2-en-1-one

Product 1

HCID 110954262-Bromo-3-methoxycyclopent-2-enoneYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 7A (500 mg, 4.46 mmol) and N-bromosuccinimide (794 mg, 4.46 mmol) in dichloromethane (5 mL) was stirred at 25° C. for 16 hours. The mixture was concentrated in vacuo. The residue was purified on a silica column (dichloromethane/methanol=200:1, v/v) to afford the title compound (650 mg, 3.40 mmol, 76% yield) as a solid. 1H NMR (400 MHz, CDCl3) δ ppm 4.12 (s, 3H), 2.79-2.82 (m, 2H), 2.62-2.65 (m, 2H); LC/MS (ESI) m/z 191 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified on a silica column (dichloromethane/methanol=200:1

Sources & evidence

ORD record
ord-81aa45cee33a4de58fcc0461cf845c06
Source dataset
uspto-grants-2016_07
Patent number
US09394279B2

Reaction notes

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