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

A 50 mL 3-neck round bottle flask was equipped with condenser, an addition funnel and a thermometer. Charge 2 g of 1,1-cyclopropyldimethanol, 5 g of acetic anhydride, 2 mL of methylene chloride and 0.77 g of pyridine to the flask. The reaction mixture was heated to about 90˜95° C. and kept continuous stirring about 1 hour. When the reaction was completed, the mixture was cooled and the 14.4 g of 33% HBr in glacial acetic acid was added while maintain below 20° C. After the addition, the reaction mixture was stirred about 6 hours and then 2 mL of methylene chloride and 10 mL of water was added into the flask. The layers were separated and the aqueous layer was extracted twice with 4 mL of methylene chloride. Combined the organic layers and washed twice with 6 mL of water and then neutralized to pH=8 with sodium carbonate solution. The organic layers were concentrated to obtain 3.3 g of crude [1-(bromomethyl)cyclopropyl]methyl acetate.

1. customA 50 mL 3-neck round bottle flask was equipped with condenser, an addition funnel
2. temperatureThe reaction mixture was heated to about 90˜95° C.
3. temperaturethe mixture was cooled
4. temperaturewhile maintain below 20° C
5. additionAfter the addition
6. stirringthe reaction mixture was stirred about 6 hours
7. customThe layers were separated
8. extractionthe aqueous layer was extracted twice with 4 mL of methylene chloride
9. washwashed twice with 6 mL of water
10. concentrationThe organic layers were concentrated

ORD record

ord-7882bd122eb841a5beebd2f886fcadee

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07271268B1