t-Butyl bromide → 13,13-Dimethyltetradecyl bromide
Reaction equation
[C:1](Br)([CH3:4])([CH3:3])[CH3:2].[Mg:6].[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][Br:20]>O1CCCC1>[C:1]([Mg:6][Br:7])([CH3:4])([CH3:3])[CH3:2].[CH3:2][C:1]([CH3:4])([CH3:3])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][Br:20]Participants
6
Reactant 3
Product 2
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
A solution of t-butylmagnesium bromide is prepared by reacting 13.7 g. of t-butyl bromide with 2.67 g. of magnesium turnings in 50 ml. dry tetrahydrofuran. The solution of Grignard reagent is dropwise added to a stirred, cold (-10° C.) solution of 36.1 g. of 1,12-dibromododecane and 0.2 g. of dilithiumetetrachlorocuprate in 75 ml. dry tetrahydrofuran at a rate such that the reaction temperature does not exceed -50° C. After one additional hour of stirring at -10° C., the solvent is evaporated and the resultant liquid is fractionated in vacuo to yield 13,13-dimethyltetradecyl bromide as a colorless liquid.
Workup
- customdoes not exceed -50° C
- customthe solvent is evaporated
Sources & evidence
- ORD record
- ord-8f1a9908aa924e0c83cea690f6e72d63
- Source dataset
- uspto-grants-1982_09
- Patent number
- US04348399
Reaction notes
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