Uses
(Bromomethyl)cyclopropane is used in the synthesis of 1,4-dienes by iron-catalyzed cross-coupling with alkenyl Grignard reagents.
Description
(Bromomethyl) cyclopropane is a cyclopropane derivative. It can be used as a synthetic building block for the introduction of the cyclopropylmethyl group. It was also used in the synthesis of 1, 4-dienes via iron-catalyzed cross-coupling with alkenyl Grignard reagents.
Chemical Properties
Colorless to yellow liquid
Uses
(Bromomethyl)cyclopropane was used as a synthetic building block for the introduction of the cyclopropylmethyl group. It was also used in the synthesis of 1,4-dienes via iron-catalyzed cross-coupling with alkenyl Grignard reagents.
General Description
The coupling reaction of (bromomethyl)cyclopropane with phenylmagnesium bromide was studied.
Synthesis
Example 1 (control experiment): 1250 mL of dimethylformamide (DMF) was added to the reaction vessel under nitrogen protection, followed by 280.8 g of triphenylphosphine. 70 g of hydroxymethylcyclopropane was added with stirring and the reaction was carried out at room temperature for 30 minutes. After cooling the reaction solution to -10°C, 158.3 g of bromine (102% of the theoretical amount) was slowly added dropwise over a period of 4 hours. Upon completion of the reaction, the reaction mixture was purified by distillation to afford bromomethylcyclopropane in 77.5% yield (based on theoretical values) with a product purity of >97%, which contained 0.6% open-chain haloalkanes.
References
[1] Patent: US6008420, 1999, A
[2] Patent: US2016/355452, 2016, A1. Location in patent: Paragraph 0062; 0063
[3] Synthetic Communications, 1996, vol. 26, # 6, p. 1109 - 1115
[4] Journal of the Chemical Society, Chemical Communications, 1982, # 18, p. 1037 - 1039
[5] European Journal of Medicinal Chemistry, 1980, vol. 15, # 6, p. 571 - 573
