1-Bromo-3-methylbutane → 15-Methylhexadecyl bromide

HRID 262927Notes

Reaction equation

HRID 262927 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][CH2:20][Br:21]>O1CCCC1>[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4][Mg:7][Br:8].[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][Br:21]

Participants

6

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 187661,12-DibromododecaneHCID 5462224Magnesium

Product 2

HCID 2043738515-Methylhexadecyl bromideHCID 178418529HCID 178418529, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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. dry tetrahydrofuran. The resultant Grignard reagent is dropwise added to a cold (-10° C.) solution of 36.1 g. of 1,12-dibromododecane and 0.2 g. of Li2CuCl4 in 75 ml. dry tetrahydrofuran. The solution is stirred for 1 hour, evaporated, and fractionally distilled in vacuo to yield 15-methylhexadecyl bromide as a colorless liquid.

Workup

  1. additionby treating 15.1 g
  2. customevaporated
  3. distillationfractionally distilled in vacuo

Sources & evidence

ORD record
ord-cd4c6d30f3f24615942e2a033a4ac304
Source dataset
uspto-grants-1979_05
Patent number
US04154756

Reaction notes

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