Hydrochloric Acid → 1-Bromo-2-ethoxyhexane

HRID 126739Notes

Reaction equation

HRID 126739 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 4N 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-366e9ff7787643498b6dc243d2ff5378
Source dataset
uspto-grants-1981_03
Patent number
US04254036

Reaction notes

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