7051-34-5

Raw materials And Preparation Products

Hazard Information

Chemical Properties

Colorless to yellow liquid

Synthesis Reference(s)

Tetrahedron Letters, 13, p. 2135, 1972 DOI: 10.1016/S0040-4039(01)84787-0

General Description

The coupling reaction of (bromomethyl)cyclopropane with phenylmagnesium bromide was studied.

Synthesis

2516-33-8

7051-34-5

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

Material Safety Data Sheet(MSDS)

Questions And Answer

• Uses

  (Bromomethyl)cyclopropane is used in the synthesis of 1,4-dienes by iron-catalyzed cross-coupling with alkenyl Grignard reagents.

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• 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. ;

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