Diiodomethane → 959749-02-1

To a solution of methyl 5-chloro-2-(vinyloxy)benzoate in 100 mL dichloromethane was added diethylzinc (1 M hexanes solution) (200 mL, 0.2 mol) under N2 atmosphere. The solution was cooled in an ice bath and a solution of trifluoroacetic acid (16 mL) in dichloromethane (100 mL) was dropped very slowly into the mixture. After stirring for 20 minutes, a solution of CH2I2 (16.4 mL, 0.2 mol) in dichloromethane (100 mL) was added dropwise. After stirring an additional 20 minutes, a solution of methyl 5-chloro-2-(vinyloxy)benzoate (21.3 g, 0.1 mol) in dichloromethane (100 mL) was added and the ice bath was removed. 8 hours later, the mixture was quenched with saturated NH4Cl solution and extracted twice with dichloromethane. The combined organics were dried over Na2SO4, filtered and evaporated to dryness to afford 21 g (92%) of methyl 5-chloro-2-cyclopropoxybenzoate. 1H NMR (400 MHz, CDCl3) δ: 7.75 (d, 1H), 7.43 (q, 1H), 3.86 (s, 3H), 3.80 (m, 1H), 0.85 (m, 4H).

1. temperatureThe solution was cooled in an ice bath
2. stirringAfter stirring an additional 20 minutes
3. customthe ice bath was removed
4. custom8 hours later, the mixture was quenched with saturated NH4Cl solution
5. extractionextracted twice with dichloromethane
6. dry with materialThe combined organics were dried over Na2SO4
7. filtrationfiltered
8. customevaporated to dryness

ORD record

ord-f6c30ed52750472a92ca1a2d4606b882

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999998B2