Hydrochloric Acid → 1-Bromo-2-ethoxyhexane

HRID 1995451Notes

Reaction equation

HRID 1995451 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH3:4].[Br:7][CH2:8][CH:9](Br)[O:10][CH2:11][CH3:12].O.Cl>CCOCC>[Br:7][CH2:8][CH:9]([O:10][CH2:11][CH3:12])[CH2:1][CH2:2][CH2:3][CH3:4]

Participants

6

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 1.68 moles of n-butylmagnesium bromide, as a 1.7 M solution in ether, is added dropwise a solution of 300 g. of 1,2-dibromo-2-ethoxyethane in 750 ml. of ether during a period of 2 hours at -15° C. The resulting mixture is stirred for one hour while warming to 20° C., then cooled to 0° C., and treated while stirring with 500 ml. of water, followed by 100 ml. of 4 N hydrochloric acid. The organic layer is washed with brine, dried over magnesium sulfate and concentrated. The residue is distilled to provide a colorless liquid, b.p. 83°-84° C., 18 mm.

Workup

  1. temperaturecooled to 0° C.
  2. additiontreated
  3. stirringwhile stirring with 500 ml
  4. washThe organic layer is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. distillationThe residue is distilled
  8. customto provide a colorless liquid, b.p. 83°-84° C., 18 mm

Sources & evidence

ORD record
ord-9bb8cb5db8f943f896de7128be13c121
Source dataset
uspto-grants-1983_09
Patent number
US04404393

Reaction notes

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