Diiodomethane → rac-(1R,2R)-2-(4-chlorophenyl)cyclopropane-1-carboxylic acid

A mixture of zinc dust (6.54 g, 0.1 mole) and cuprous chloride (1 g, 0.01 mole) in methylene chloride (30 mL) is stirred and heated to reflux under a nitrogen atmosphere for 30 min. After the mixture is cooled to room temperature, methylene iodide (13.4 g, 0.05 mole) is added to the mixture which is then refluxed for an additional hour. After cooling to 0° C., trans-4-chlorocinnamic acid (9.1 g) is added. The reaction is allowed to warm to room temperature over 2 hours and then refluxed for 3 days. The reaction is quenched at 0° C. by the addition of 30 ml of diethyl ether and 30 ml of ice cold 10% H2SO4 solution. The mixture is filtered washed with ether. The organic layer is dried over MgSO4 and concentrated to provide the desired product as a white solid. 1H NMR (CDCl3) 7.25 (d, J=7 Hz, 2H), 7.05 (d, J=7 Hz, 2H) , 2.58 (m, 1H), 1.85 (m, 1H), 1.65 (m, 1H), 1.37 (m, 1H).

1. temperatureheated
2. temperatureto reflux under a nitrogen atmosphere for 30 min
3. temperatureis then refluxed for an additional hour
4. temperatureAfter cooling to 0° C.
5. temperatureto warm to room temperature over 2 hours
6. temperaturerefluxed for 3 days
7. customThe reaction is quenched at 0° C. by the addition of 30 ml of diethyl ether and 30 ml of ice cold 10% H2SO4 solution
8. filtrationThe mixture is filtered
9. washwashed with ether
10. dry with materialThe organic layer is dried over MgSO4
11. concentrationconcentrated

ORD record

ord-03d6b878dee54416b74703a33d9cc63a

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06544996B2