Hydrogen Bromide → [1-(Bromomethyl)cyclopropyl]methyl acetate

A 3 L 3-neck round bottle flask was equipped with mechanical stirrer, a thermometer, a nitrogen inlet and an additional funnel. To the flask was charged 200 g of 1,1-cyclopropyldimethanol and 200 mL of methylene chloride. The mixture was cooled to 0˜5° C. 1440 g of 33% HBr in glacial acetic acid was slowly added to reaction solution and kept the temperature below 20° C. After the addition, the reaction mixture was stirred at between 10° C. and 18° C. for about 2 hours and then warmed to 16˜22° C. and stirred about 1 hour. When the starting material of 1,1-cyclopropyldimethanol was disappeared (checked by TLC, mobile phase:EA/hx=1/3(V/V)), 1000 mL of water was added to the reaction mixture with stirring over 30 min and kept the temperature below 20° C. The layers were separated and the aqueous layer was back extracted with 300 mL methylene chloride. To the combined organic layers was added 400 ml of water, and then was neutralized to pH 6˜7 with 10% NaOH aqueous solution. The organic layers were concentrated to obtain 396 g of crude [1-(bromomethyl)cyclopropyl]methyl acetate.

1. customA 3 L 3-neck round bottle flask was equipped with mechanical stirrer
2. temperatureThe mixture was cooled to 0˜5° C
3. customthe temperature below 20° C
4. additionAfter the addition
5. temperaturewarmed to 16˜22° C.
6. stirringstirred about 1 hour
7. additionwas added to the reaction mixture
8. stirringwith stirring over 30 min
9. customthe temperature below 20° C
10. customThe layers were separated
11. extractionthe aqueous layer was back extracted with 300 mL methylene chloride
12. additionTo the combined organic layers was added 400 ml of water
13. concentrationThe organic layers were concentrated

ORDレコード

ord-386f37afdb8e4c4280beb6e5b5382e90

出典データセット

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07271268B1