Bromine → 4-[1-(5-Bromofuran-2-yl)ethyl]morpholine

HRID 606574Notes

Reaction equation

HRID 606574 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[CH3:7].S([O-])([O-])(=O)=S.[Na+].[Na+].[Br:21]Br>C(Cl)Cl>[Br:21][C:5]1[O:1][C:2]([CH:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH3:7])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 141200674-(1-Furan-2-yl-ethyl)-morpholine

Product 1

HCID 670466564-[1-(5-Bromofuran-2-yl)ethyl]morpholineYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4-(1-furan-2-yl-ethyl)-morpholine (1.1 mmol) was taken up in DCM (5 ml) and stirred at 0° C. Nitrogen was passed through the reaction vessel and bubbled out through a Dreschel bottle containing a saturated aqueous solution of sodium thiosulphate, whilst bromine (1.54 mmol in 2 ml DCM) was added dropwise. After addition the reaction was stirred at room temperature for 2 h, then diluted with more DCM, washed twice with 2M Na2CO3 solution, dried over Na2SO4 and concentrated in-vacuo. After purification by flash chromatography (silica, 5 to 10% EtOAc in hexane), 4-[1-(5-bromo-furan-2-yl)-ethyl]-morpholine was obtained as a golden oil: m/z in MS ES+=260, 262 [M+H]+, 0.46 mmol, 42% yield.

Workup

  1. custombubbled out through a Dreschel bottle
  2. additionwas added dropwise
  3. additionAfter addition the reaction
  4. stirringwas stirred at room temperature for 2 h
  5. washwashed twice with 2M Na2CO3 solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in-vacuo
  8. customAfter purification by flash chromatography (silica, 5 to 10% EtOAc in hexane)

Sources & evidence

ORD record
ord-06fefb656ed6488594998b2bd3eaf68a
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

Loading…