1,11-Dibromoundecane → Pentadecane, 1-bromo-14-methyl-

HRID 1105699Notes

Reaction equation

HRID 1105699 reaction equation
[CH3:1][CH:2]([CH3:7])[CH2:3][CH2:4][Mg]Br.[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>O1CCCC1.[Cu](Cl)Cl.[Li]>[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:4][CH2:3][CH:2]([CH3:7])[CH3:1]

Participants

5

Reactant 2

HCID 855511,11-DibromoundecaneHCID 178418529HCID 178418529, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 86737138Lithium copper chlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

By a procedure analogous to that described above, 3-methylbutyl magnesium bromide in tetrahydrofuran is reacted with 34.5 g. (0.11 moles) 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. customis reacted with 34.5 g
  2. customthe solution is evaporated
  3. distillationthe resultant oil is distilled in vacuo

Sources & evidence

ORD record
ord-938313edfceb40c0a40f81f7cf67e653
Source dataset
uspto-grants-1982_01
Patent number
US04309553

Reaction notes

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