ChemicalBook CAS DataBase List 2-Bromoadamantane

2-Bromoadamantane synthesis

11synthesis methods

Product Name:2-Bromoadamantane
CAS Number:7314-85-4
Molecular formula:C10H15Br
Molecular Weight:215.13

281-23-2
493 suppliers
$5.00/25g

768-90-1 Synthesis

768-90-1
409 suppliers
$10.00/5g

7314-85-4
163 suppliers
$18.00/1g

876-53-9
245 suppliers
$25.00/5g

Yield:768-90-1 35 %Spectr. ，7314-85-4 14 %Spectr. ，876-53-9 11 %Spectr.

Reaction Conditions:

with tert-butyl hypobromite;carbon tetrabromide in dichloromethane at 40; for 90 h;Darkness;Reagent/catalyst;

Steps:

Table S2, entry 3
tert-Butyl hypobromite 50 (0.33 mL, freshly prepared and used immediately, 0.05 mmol, 0.1 eq.), adamantane 18 (68 mg, 0.5 mmol), carbon tetrabromide (166 mg, 0.5 mmol, 1 eq.) and dichloromethane (3.13 mL) were added to an oven-dried pressure tube and the reaction mixture was stirred at 40 °C for 90 h in the dark. The reaction mixture was cooled to RT and quenched with aqueous hydrochloric acid (1 M, 5 mL) and extracted with dichloromethane (4 x 10 mL). The organic phases were combined, dried over Na2SO4, filtered and concentrated in vacuo. The yield of adamantane 18 (29%), 1-bromoadamantane 31 (35%), 2-bromoadamantane 51 (14%) and 1,3-bromoadamantane 52 (11%) were determined by adding 1,3,5-trimethoxybenzene to the crude mixture as an internal standard for 1H-NMR.

References:

Emery, Katie J.;Young, Allan;Arokianathar, J. Norman;Tuttle, Tell;Murphy, John A. [Molecules,2018,vol. 23,# 5,art. no. 1055] Location in patent:supporting information

FullText

935-56-8 Synthesis