3-(Trifluoromethyl)phenol → 2-(3-Chloro-phenoxy)-5-fluoro-nicotinic acid

HRID 1877372Notes

Reaction equation

HRID 1877372 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:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=1>>[Cl:23][C:24]1[CH:25]=[C:26]([CH:27]=[CH:28][CH:29]=1)[O:30][C:2]1[N:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 79333-ChlorophenolHCID 114352432-Chloro-5-fluoronicotinic acid

Product 1

HCID 673673952-(3-Chloro-phenoxy)-5-fluoro-nicotinic acid

Procedure

2-(3-Chloro-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 3-chloro-phenol ([CAS RN 108-43-0]). 1H NMR (400 MHz, DMSO): δ7.09 (dd, J=8.4 Hz, J=1.6 Hz, 1H), 7.24-7.25 (m, 2H), 7.44 (t, J=8.4 Hz, 1H), 8.19 (dd, J=8.1 Hz, J=3.2 Hz, 1H), 8.37 (d, J=3.2 Hz, 1H), 13.60 (s, 1H). 19F NMR (376.5 MHz, DMSO): −134.4. MS (ISN): 266.0 [M−H]−.

Sources & evidence

ORD record
ord-5ed613fa02684f84ade9b759ca57271f
Source dataset
uspto-grants-2012_11
Patent number
US08309734B2

Reaction notes

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