Dimethyl Sulfoxide → 3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde
Reaction equation
[F:1][CH:2]([F:13])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][C:5]=1[OH:12].C([O-])([O-])=O.[K+].[K+].CS(C)=O.Br[CH2:25][CH:26]1[CH2:28][CH2:27]1>C1(C)C=CC=CC=1>[CH:26]1([CH2:25][O:12][C:5]2[CH:6]=[C:7]([CH:10]=[CH:11][C:4]=2[O:3][CH:2]([F:13])[F:1])[CH:8]=[O:9])[CH2:28][CH2:27]1Participants
Conditions
- Temperature
- 70 °C
Procedure
55 g of 4-(difluoromethoxy)-3-hydroxybenzaldehyde, 42.42 g of K2CO3 (1.05 eq), 4.86 g of KI (0.1 eq) and 220 mL of dimethylsulphoxide (DMSO) were loaded in a reactor. The mixture was heated at 70° C. and kept for 1 h. A mixture previously prepared of 42.65 g of bromomethyl cyclopropane (1.08 eq) and 110 mL of DMSO was added for 1 hour. The reaction was kept for 3 h at 70° C., and then cooled at room temperature. Once the temperature was reached, 375 mL of toluene was added. The suspension was filtered to remove the remaining K2CO3, and then it was cooled at 0-5° C., and 375 mL of deionised water were loaded. The phases were separated and the organic phase was washed twice with 55 mL of deionised water. The solvent was removed at reduced pressure, obtaining 70 g (yield 99%) of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde as a viscous yellowish fluid.
Workup
- additionwas added for 1 hour
- waitThe reaction was kept for 3 h at 70° C.
- temperaturecooled at room temperature
- filtrationThe suspension was filtered
- customto remove the remaining K2CO3
- temperatureit was cooled at 0-5° C.
- customThe phases were separated
- washthe organic phase was washed twice with 55 mL of deionised water
- customThe solvent was removed at reduced pressure
Sources & evidence
- ORD record
- ord-3b070412b6b6400db9f0c34a93d61284
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321726B2
Reaction notes
Loading…