1,10-Dibromodecane → 13-(4-Methylphenyl)tridecyl bromide

HRID 2057654Notes

Reaction equation

HRID 2057654 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10]Br)=[CH:4][CH:3]=1.[Mg:12].[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][Br:24]>O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][Mg:12][Br:13])=[CH:4][CH:3]=1.[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][Br:24])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 2214831,10-DibromodecaneHCID 5462224MagnesiumHCID 140848591-(3-Bromopropyl)-4-methylbenzene

Product 2

HCID 2033113313-(4-Methylphenyl)tridecyl bromideHCID 178424987HCID 178424987, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of 3-(4-methylphenyl)propylmagnesium bromide is prepared by reacting 20 g. 3-(4-methylphenyl)propyl bromide with 2.5 g. of magnesium turnings in 50 ml. dry tetrahydrofuran. The solution of Grignard reagent is added dropwise to a stirred, cold (-10° C.) solution of 30 g. of 1,10-dibromodecane and 0.2 g. of lithium tetrachlorocuprate in 75 ml. dry tetrahydrofuran at a rate such that the reaction temperature does not exceed -5° C. After one addition hour of stirring at -10° C., the solvent is evaporated and the resultant liquid is fractionated in vacuo to yield 13-(4-methylphenyl)tridecyl bromide as a colorless liquid.

Workup

  1. customdoes not exceed -5° C
  2. additionAfter one addition hour
  3. customthe solvent is evaporated

Sources & evidence

ORD record
ord-74432f955c1e4698b54dd2e5d5cfd342
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

Loading…