4-Methyl-2-(5-trifluoromethyl-biphenyl-3-yl)pentanoic acid → 4-Methyl-2-[4'-trifluoromethyl-5-(3-trifluoromethyl-benzyl)-biphenyl-3-yl]-pentanoic acid
Reaction equation
[CH3:1][CH:2]([CH3:24])[CH2:3][CH:4]([C:8]1[CH:9]=[C:10](C2C=CC=CC=2)[CH:11]=[C:12](C(F)(F)F)[CH:13]=1)[C:5]([OH:7])=[O:6].[Cl-].[F:26][C:27]([F:37])([F:36])[C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][Zn+]>>[CH3:24][CH:2]([CH3:1])[CH2:3][CH:4]([C:8]1[CH:9]=[C:10]([C:33]2[CH:30]=[CH:29][C:28]([C:27]([F:37])([F:36])[F:26])=[CH:35][CH:34]=2)[CH:11]=[C:12]([CH2:31][C:30]2[CH:33]=[CH:34][CH:35]=[C:28]([C:27]([F:37])([F:36])[F:26])[CH:29]=2)[CH:13]=1)[C:5]([OH:7])=[O:6]Participants
3
Procedure
The title compound was prepared from a Nigishi coupling of 4-methyl-2-(5-trifluoromethyl-biphenyl-3-yl)pentanoic acid (intermediate compound 1g) with 3-trifluoromethylbenzyl zinc chloride under the conditions described in Example 2; 1H NMR (400 MHz, MeOD) δ ppm 0.76-0.86 (m, 6 H), 1.36 (dt, J=13.51, 6.82 Hz, 1 H), 1.54-1.62 (m, 1 H), 1.80-1.91 (m, 1 H), 3.62 (t, J=7.83 Hz, 1 H), 4.05 (s, 2 H), 7.16 (s, 1 H), 7.33-7.44 (m, 6 H), 7.64 (q, J=8.56 Hz, 4 H); Calcd for C27H24F6O2 (M+Na) 517.17, Found 517.2.
Sources & evidence
- ORD record
- ord-a0d7333c3db64f8eab7857d82a9b69d0
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08692017B2
Reaction notes
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