2,5-Dichlorophenol → 2-(2,5-Dichloro-phenoxy)-5-fluoro-nicotinic acid
Reaction equation
Cl[C:2]1[N:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].FC(F)(F)C1C=C(O)C=CC=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[OH:31]>>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[O:31][C:2]1[N:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]Participants
4
Procedure
2-(2,5-Dichloro-phenoxy)-5-fluoro-nicotinic acid was prepared in analogy to Example 1, Step 1, replacing 2-chloro-nicotinic acid with 2-chloro-5-fluoro-nicotinic acid ([CAS RN 38186-88-8]) and 3-trifluoromethyl-phenol with 2,5-dichloro-phenol ([CAS RN 583-78-8]). 1H NMR (400 MHz, DMSO): δ7.38 (dd, J=8.4 Hz, J=2.4 Hz, 1H), 7.51 (d, J=2.4 Hz, 1H), 7.62 (d, J=8.4 Hz, 1H), 8.23 (dd, J=8.1 Hz, J=3.2 Hz, 1H), 8.34 (d, J=3.2 Hz, 1H), 13.65 (s, 1H). 19F NMR (376.5 MHz, DMSO): −134.6. MS (ISN): 302.0 [M−H]−.
Sources & evidence
- ORD record
- ord-24d0fea6fdf04fb48ed755ed8c4bffa3
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08309734B2
Reaction notes
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