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ChemicalBook CAS DataBase List (Bromomethyl)cyclopropane
7051-34-5

(Bromomethyl)cyclopropane synthesis

10synthesis methods
Cyclopropyl carbinol

2516-33-8

(Bromomethyl)cyclopropane

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.

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Yield:7051-34-5 77.5%

Reaction Conditions:

with bromine;triphenylphosphine in N-methyl-acetamide

Steps:

1 Example 1
Example 1 (for comparison) 1250 ml of dimethylformamide were placed into the reaction vessel, and then 280.8 g of triphenylphosphine and then 70 g of hydroxymethylcyclopropane were added, the mixture was stirred for 30 minutes at room temperature under a nitrogen atmosphere, and the solution was subsequently cooled to -10° C. Then, 158.3 g of bromine (that is to say 2 mol % more than theoretically required) were metered in in the course of 4 hours. The reaction mixture was worked up by distillation. Bromomethylcyclopropane was obtained in a yield of 77.5% of theory. The purity of the product was over 97%, the open-chain halogenoalkanes amounted to 0.6%.

References:

Bayer Aktiengesellschaft US6008420, 1999, A

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