2-(3-Chloropropyl)-2-methyl-1,3-dioxolane → 2-(3-Bromopropyl)-2-methyl-1,3-dioxolane

HRID 2059339Notes

Reaction equation

HRID 2059339 reaction equation
[CH2:1]1[O:10][C:4]([CH2:6][CH2:7][CH2:8]Cl)([CH3:5])[O:3][CH2:2]1.[Br-:11].[Li+].C(N(C(C)C)CC)(C)C>O1CCCC1>[CH2:1]1[O:10][C:4]([CH2:6][CH2:7][CH2:8][Br:11])([CH3:5])[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 800792-(3-Chloropropyl)-2-methyl-1,3-dioxolaneHCID 81531DiisopropylethylamineHCID 82050Lithium Bromide

Product 1

HCID 5600542-(3-Bromopropyl)-2-methyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.0 Parts of 5-chloro-2-pentanone ethylene ketal is mixed with 9.0 parts of lithium bromide and 2.0 parts of diisopropylethylamine in 30 parts by volume of tetrahydrofuran which has been distilled from lithium aluminum hydride. The mixture is refluxed under nitrogen for 48 hours, cooled and poured into a mixture of ether and water for extraction. The ether layer is washed twice with water, then with 1 N hydrochloric acid and then twice again with water. The ether layer is then dried over sodium sulfate and evaporated under reduced pressure to give 5-bromo-2-pentanone ethylene ketal of formula XXI of Chart C.

Workup

  1. distillationhas been distilled from lithium aluminum hydride
  2. temperatureThe mixture is refluxed under nitrogen for 48 hours
  3. temperaturecooled
  4. additionpoured into a mixture of ether and water for extraction
  5. washThe ether layer is washed twice with water
  6. dry with materialThe ether layer is then dried over sodium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ee2e276032a7465194dc974d38a2eeb1
Source dataset
uspto-grants-1982_03
Patent number
US04322543

Reaction notes

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