Chlorodifluoromethane → 4-(5-Difluoromethoxy-3-trifluoromethyl-pyrazol-1-yl)-benzoic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([OH:16])=[CH:14][C:13]([C:17]([F:20])([F:19])[F:18])=[N:12]2)=[CH:7][CH:6]=1)[CH3:2].[F:22][CH:23]([F:25])Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15]([O:16][CH:23]([F:25])[F:22])=[CH:14][C:13]([C:17]([F:20])([F:18])[F:19])=[N:12]2)=[CH:9][CH:10]=1)[CH3:2]Participants
5
Conditions
- Temperature
- -78 °C
Procedure
A mixture of 4-(5-hydroxy-3-trifluoromethyl-pyrazol-1-yl)-benzoic acid ethyl ester (1 g, 3.3 mmol), difluorochloromethane (3 g, 34 mmol) and potassium carbonate (0.5 g, 3.6 mmol) in DMF (9 mL) was stirred in a sealed tube at −78° C. for 3 minutes and then at 100° C. for 12 hours. The mixture was cooled to −78° C. and the precipitate was removed by filtration and washed with DMF (3×1 mL). The filtrate and washings were poured into cold water (200 mL). The resulting suspension was transferred into a centrifuge tube and the contents were centrifuged at room temperature for 10 minutes and filtered to give 4-(5-difluoromethoxy-3-trifluoromethyl-pyrazol-1-yl)-benzoic acid ethyl ester (1.1 g, 94% yield) as a yellow solid.
Workup
- waitat 100° C. for 12 hours
- temperatureThe mixture was cooled to −78° C.
- customthe precipitate was removed by filtration
- washwashed with DMF (3×1 mL)
- additionThe filtrate and washings were poured into cold water (200 mL)
- customThe resulting suspension was transferred into a centrifuge tube
- waitthe contents were centrifuged at room temperature for 10 minutes
- filtrationfiltered
Sources & evidence
- ORD record
- ord-87b2e5c34093474db4f5339e73fb4c12
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07202232B2
Reaction notes
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