ChemicalBook CAS DataBase List NEOPENTYLBENZENE

NEOPENTYLBENZENE synthesis

11synthesis methods

Product Name:NEOPENTYLBENZENE
CAS Number:1007-26-7
Molecular formula:C11H16
Molecular Weight:148.24

15501-33-4
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$15.00/1g

100-58-3
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$18.00/10ml

1007-26-7
96 suppliers
$36.79/5g

Yield: 15 %Chromat.

Reaction Conditions:

Stage #1:phenylmagnesium bromide with zinc(II) chloride in tetrahydrofuran at -20; for 0.25 h;Inert atmosphere;
Stage #2: with methylmagnesium chloride in tetrahydrofuran at -20; for 0.25 h;Inert atmosphere;
Stage #3:neopentyl iodide with triphenylphosphine;nickel dichloride in tetrahydrofuran at 0 - 20; for 1 h;Inert atmosphere;regioselective reaction;

Steps:

Typical procedure for the coupling of methylarylzincs with primary alkyl iodides:
General procedure: All reactions were carried out in oven-dried glassware under a positive pressure of nitrogen using standard syringe-septum cap techniques.²⁸ For the preparation of methylarylzinc reagents (aryl: C₆H₅, MeC₆H₄, MeOC₆H₄), arylzinc chlorides were reacted with methylmagnesium chloride. Arylzinc chloride was prepared by addition of arylmagnesium bromide (2 mmol) to ZnCl₂ (2 mmol) in THF (4 ml) at -20 °C and stirring at that temperature for 15 min. To freshly prepared arylzinc chloride (2 mmol), methylmagnesium chloride (2 mmol) was added and the mixture was stirred at -20 °C for another 15 min. For the preparation of methylarylzinc reagents (aryl: 4-MeCOC₆H₄, 3-MeCOC₆H₄), arylmagnesium bromides were reacted with methylzinc chloride.²⁶ Arylmagnesium bromide (2 mmol) was prepared by addition of isopropylmagnesium bromide (2.1 mmol) to a solution of aryl iodide (2 mmol) in THF (4 ml) at -15 °C and stirring at that temperature for 1 hour to complete the Br/Mg exchange.²⁹ Arylmagnesium bromide (2 mmol) solution was added to methylzinc chloride (2 mmol), freshly prepared by addition of methylmagnesium bromide (2 mmol) to ZnCl₂ (2 mmol) in THF (4 ml) at -20 °C and the mixture was stirred at that temperature for 15 min. For the alkyl coupling reaction of methylarylzincs, a mixture of NiCl₂ (10 mol %, 0.013 g), PPh₃ (10 mol %, 0.0263) and primary alkyl iodide in THF (2 ml) was cooled to 0 °C and freshly prepared methylarylzinc (2 mmol) was added slowly. The reaction mixture was stirred at room temperature for 1 h and then hydrolyzed by addition of 1 M HCl and subsequently extracted with Et₂O. The combined ethereal solutions were washed with aq NaHCO₃ solution, dried and aliquots were analyzed by GC.