2-Phenyl-2-bromopropane: A solution of 33 g of PBr3 (0.12 mol) in 55 mL of chloroform was added dropwise at 40 C to a stirred solution of 50 g of a,a-dimethylbenzyl alcohol (0.36 mol) in 700 mL of chloroform.The reaction mixture was stirred for 2 h at 40 C. The chloroform layer was separated from the viscous inorganic layer and poured into 500 mL of ice water. The organic layer was separated, washed twice with a saturated aqueous Na
2CO
3 solution and once with water, and dried over MgSO
4. The chloroform was removed under reduced pressure. After distillation a colorless liquid was obtained; boiling region 57-80 C (0.05 mmHg). The product contained 31% of the elimination product a-methylstyrene. The product was used without further purification for the synthesis of lf. The yield of 2-phenyl-2-bromopropane was
57%a,a-Dimethylbenzylamine: This amine was obtained by treatment of 2-phenyl-2-bromopropane with liquid ammonia.
* After evaporation of the ammonia, the product was dissolved in 1 M aqueous HCl and the a-methylstyrene was extracted with diethyl ether. The water layer was brought to pH 14, and the free amine was extracted with ether. The ether layer was dried over MgSO
4, and the ether removed under reduced pressure. The yield was
53%*: Brander, M. M. Red. Trm. Chim. Puys-Bus Belg. 1918,37,76-87.I agree, the yields are not the best..
Alcohols/Alkenes to chlorides:
A Convenient Procedure for the Quantitative Conversion of Reactive Alcohols and Olefins into the Corresponding Chlorides Herbert C. Brown, Min-Hon Rei;
J. Org. Chem.; 1966; 31(4); 1090-1093.
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..and refs in there.