Sodium Iodide → 3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]([F:13])[F:12])=[C:6]([OH:14])[CH:5]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].Br[C:25]1([CH3:28])[CH2:27][CH2:26]1>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]([F:12])[F:13])=[C:6]([O:14][CH2:28][CH:25]2[CH2:27][CH2:26]2)[CH:5]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
3-hydroxy-4-(difluoromethoxy)-benzoic acid methyl ester (5 g, 22.9 mmol), K2CO3 (4.75 g, 34.4 mmol), NaI (0.34 g, 2.3 mmol) and bromo-methylcyclopropane (3.7 g, 27.5 mmol) were dissolved in DMF (25 ml), and the heterogeneous mixture was stirred and warmed at 80° C. for two hours. The suspension was cooled to room temperature, and water (50 ml) was added under stirring. The heterogeneous mixture was cooled to 0 to 5° C. for 60 to 90 minutes, and the solid filtered on a gooch funnel and washed with water (50 ml). An orange solid was obtained. It was dried under vacuum at room temperature. (yield 95.8%).
Workup
- temperatureThe suspension was cooled to room temperature
- stirringunder stirring
- temperatureThe heterogeneous mixture was cooled to 0 to 5° C. for 60 to 90 minutes
- filtrationthe solid filtered on a gooch funnel
- washwashed with water (50 ml)
- customAn orange solid was obtained
- customIt was dried under vacuum at room temperature
Sources & evidence
- ORD record
- ord-c4265732d68d4518b7948f2f6db5f8ab
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434691B2
Reaction notes
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