Diethyl Ether → 325465-53-0

HRID 1811361Notes

Reaction equation

HRID 1811361 reaction equation
C(OCC)C.[CH2:6]([C:8]1[O:9][C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[CH:12]=1)[CH3:7].[Br:17]Br>C(OCC)(=O)C>[Br:17][C:12]1[C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[O:9][C:8]=1[CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24408BromineHCID 765822-Ethylbenzofuran

Product 1

HCID 3790709325465-53-0

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a 250 mL flask equipped with magnetic stirring is added 100 mL of diethyl ether and 2-ethylbenzofuran (20.00 g, 136.8 mmol). The reaction flask is cooled to 0° C. and bromine (8.40 mL, 164.2 mmol) is added to an addition funnel containing 50 mL of ethyl acetate. The mixture is added dropwise to the reactor while maintaining the 0° C. temperature. The addition funnel is rinsed with an additional 20 mL of ethyl acetate. The resulting mixture is stirred for 2 hours and the temperature maintained at 0° C. The reaction is quenched with 50 mL of water. The contents of the reactor are then transferred to a 1 L separatory funnel and rinsed with 2×50 mL of water. The organic layers are combined and rinsed with 200 mL of a saturated sodium thiosulfate solution. The layers are separated and the organic layer is dried over MgSO4 to give an amber colored solution. The solvent is removed in vacuo to give the product, 3-bromo-2-ethylbenzofuran, as a pale yellow liquid which is used without further purification (yield: 27.1 g, 88 percent).

Workup

  1. customTo a 250 mL flask equipped
  2. additionThe mixture is added dropwise to the reactor
  3. temperaturewhile maintaining the 0° C. temperature
  4. washThe addition funnel is rinsed with an additional 20 mL of ethyl acetate
  5. stirringThe resulting mixture is stirred for 2 hours
  6. temperaturethe temperature maintained at 0° C
  7. customThe reaction is quenched with 50 mL of water
  8. customThe contents of the reactor are then transferred to a 1 L separatory funnel
  9. washrinsed with 2×50 mL of water
  10. washrinsed with 200 mL of a saturated sodium thiosulfate solution
  11. customThe layers are separated
  12. dry with materialthe organic layer is dried over MgSO4
  13. customto give an amber colored solution
  14. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-531f18686b0c4bc090ffa6103b6e4f97
Source dataset
uspto-grants-2013_01
Patent number
US08362265B2

Reaction notes

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