1-Bromo-3-methylbutane → Pentadecane, 1-bromo-14-methyl-

HRID 1764716Notes

Reaction equation

HRID 1764716 reaction equation
[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4]Br.[Mg:7].[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][Br:20]>[Cu](Cl)Cl.[Li].O1CCCC1>[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4][Mg:7][Br:8].[Br:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:4][CH2:3][CH:2]([CH3:6])[CH3:1]

Participants

7

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 855511,11-DibromoundecaneHCID 5462224Magnesium

Product 2

HCID 10881292Pentadecane, 1-bromo-14-methyl-HCID 178418529HCID 178418529, compound

Reagents, catalysts & solvents 2

HCID 86737138Lithium copper chlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of 3-methylbutylmagnesium bromide is prepared by treating 15.1 g. of 3-methylbutyl bromide with 2.7 g. of magnesium turnings in 50 ml. of dry tetrahydrofuran. The resultant Grignard reagent is added dropwise to a solution of 34.5 g. of 1,11-dibromoundecane and 0.2 g. of lithium copper chloride in 75 ml. of tetrahydrofuran. After 1 hour stirring at -10° C., the solution is evaporated, and the resultant oil is distilled in vacuo to yield the colorless 1-bromo-14-methylpentadecane.

Workup

  1. additionby treating 15.1 g
  2. customthe solution is evaporated
  3. distillationthe resultant oil is distilled in vacuo

Sources & evidence

ORD record
ord-83c3c34cfffb4fb2814e4dd664139c76
Source dataset
uspto-grants-1978_09
Patent number
US04117158

Reaction notes

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