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

HRID 1106288Notes

Reaction equation

HRID 1106288 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 grams of 5-chloro-2-pentanone ethylene ketal is mixed with 9.0 grams of lithium bromide and 2.0 grams of diisopropylethylamine in 30 ml 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 title product.

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-045cd49e555340efa01e591f3b47857e
Source dataset
uspto-grants-1982_01
Patent number
US04312994

Reaction notes

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