N-bromobutanimide → HCID 66926140, compound

HRID 2170799Notes

Reaction equation

HRID 2170799 reaction equation
[CH3:1][O:2][C:3]1[CH2:7][CH:6]([CH2:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5](=[O:15])[CH:4]=1.[Br:16]N1C(=O)CCC1=O>ClCCCl>[Br:16][C:4]1[C:5](=[O:15])[CH:6]([CH2:8][CH:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[CH2:7][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66926043HCID 66926043, compound

Product 1

HCID 66926140HCID 66926140, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-methoxy-5-(tetrahydro-pyran-4-ylmethyl)-cyclopent-2-enone (906 mg, 4.7 mmol) in 1,2-dichloroethane (15 ml) at 0° C. in an amber flask was added portion wise over one hour N-bromosuccinimide (890 mg, 5 mmol). The reaction was stirred at 0° C. for a further 90 minutes and then any remaining solid was removed by filtration. The filtrate was evaporated to dryness under reduced pressure, the resultant solid dissolved in warm toluene (50 ml) and washed quickly with ice-cold water (2×20 ml). The organic phase was dried over magnesium sulfate and the solvent evaporated in vacuo. The residue was purified using column chromatography (40% to 80% EtOAc in hexane) to give 2-bromo-3-methoxy-5-(tetrahydro-pyran-4-ylmethyl)-cyclopent-2-enone (1.1 g).

Workup

  1. customany remaining solid was removed by filtration
  2. customThe filtrate was evaporated to dryness under reduced pressure
  3. dissolutionthe resultant solid dissolved in warm toluene (50 ml)
  4. washwashed quickly with ice-cold water (2×20 ml)
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customthe solvent evaporated in vacuo
  7. customThe residue was purified

Sources & evidence

ORD record
ord-d1b99577c80b43048afb52d9e786176b
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

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