Carbon Tetrachloride → 1-(Bromomethyl)-3-tert-butylbenzene
Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br:12]N1C(=O)CCC1=O.C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>CCCCCC>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[CH2:11][Br:12])([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A dry 100 mL 3-necked flask equipped with a nitrogen inlet, a condenser, a thermometer, and a magnetic stirrer was charged with 2.0 g of 3-tert-butyltoluene (Wiley Organics, Coshocton, Ohio 43812), 2.40 g of N-bromosuccinimide (Aldrich), and 30 mL of CCl4. The mixture was treated with 0.16 g of benzoyl peroxide (Aldrich) and heated at 6-° C. under N2. Careful temperature control is important to minimize by-product formation. After 1 h at 60° C. the reaction mixture was cooled to 0° C., filtered to remove succinimide, and the filtrate was concentrated in vacuo to afford a light yellow liquid. Analysis of this material by tlc (SiO2, hexane) indicated a major new component at Rf =0.50, a minor component at Rf =0.55, and a trace of 3-tert-butyltoluene at Rf =0.75. The crude product was purified by flash chromatography on 100 g of silica gel (hexane) to afford 1.06 g (35%) of 3-tert-butylbenzyl bromide as a clear liquid.
Workup
- customA dry 100 mL 3-necked flask equipped with a nitrogen inlet, a condenser
- temperatureheated at 6-° C
- filtrationfiltered
- customto remove succinimide
- concentrationthe filtrate was concentrated in vacuo
- customto afford a light yellow liquid
- customThe crude product was purified by flash chromatography on 100 g of silica gel (hexane)
Sources & evidence
- ORD record
- ord-899c5ad1c9a44de4b6fb8f74dff97171
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06140100
Reaction notes
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