Hydrochloric Acid → HCID 73052801, compound

Temperature

-50 °C

207.2 g crude (1-chlorocarbonylmethyl-cyclopropyl)-acetic acid methyl ester (approx. 1.07 mole, 97% purity, from step 4) are dissolved in 1428 ml of a 3:1 mixture of tetrahydrofuran and toluene. The mixture is cooled to −50° C. and 6.3 g of iron(III)bromide (0.02 mole, 0.02 eq) are added. Then 357 ml of methylmagnesium chloride in tetrahydrofuran (3 M solution in tetrahydrofuran, 1.07 mole, 1.0 eq) are added dropwise over two hours. After in-process control another 55 ml of methylmagnesium chloride in tetrahydrofuran (3 M solution in tetrahydrofuran, 0.17 mole, 0.15 eq) are added dropwise. Stirring is continued for 40 min, then the mixture is warmed to approx. 0° C., and diluted with 750 ml of methyl tert-butyl ether. Then the mixture is transferred onto a mixture of 27 ml of 37% hydrochloric acid and 480 ml of water. The phases are separated and the aqueous phase is extracted with 480 ml of methyl tert-butyl ether. The combined organic phases are washed twice with 480 ml of water (each) and then with 210 ml of brine, then dried over magnesium sulfate and evaporated to dryness to yield a dark red/brown oil.

1. temperaturethe mixture is warmed to approx. 0° C.
2. customThe phases are separated
3. extractionthe aqueous phase is extracted with 480 ml of methyl tert-butyl ether
4. washThe combined organic phases are washed twice with 480 ml of water (each) and then with 210 ml of brine
5. dry with materialdried over magnesium sulfate
6. customevaporated to dryness
7. customto yield a dark red/brown oil

ORD record

ord-b9676a4d7d904197a7a23a950ad13b8a

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09212120B2