[5-Methoxy-2-methyl-4-(3-methyl-4'-trifluoromethyl-biphenyl-4-ylmethylsulfanyl)-phenoxy]-acetic acid methyl ester → [5-Methoxy-2-methyl-4-(3-methyl-4'-trifluoromethyl-biphenyl-4-ylmethylsulfanyl)-phenoxy]-acetic acid

HRID 1591553Notes

Reaction equation

HRID 1591553 reaction equation
CC1C=C(C2C=CC(C(F)(F)F)=CC=2)C=CC=1CO.C[O:21][C:22](=[O:53])[CH2:23][O:24][C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([S:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]3[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][CH:42]=3)=[CH:37][C:36]=2[CH3:51])=[CH:27][C:26]=1[CH3:52]>>[CH3:32][O:31][C:29]1[C:28]([S:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]3[CH:46]=[CH:45][C:44]([C:47]([F:49])([F:50])[F:48])=[CH:43][CH:42]=3)=[CH:37][C:36]=2[CH3:51])=[CH:27][C:26]([CH3:52])=[C:25]([CH:30]=1)[O:24][CH2:23][C:22]([OH:53])=[O:21]

Participants

3

Reactant 2

HCID 20827046[5-Methoxy-2-methyl-4-(3-methyl-4'-trifluoromethyl-biphenyl-4-ylmethylsulfanyl)-phenoxy]-acetic acid methyl ester2×HCID 22280004[3-Methyl-4'-(trifluoromethyl)biphenyl-4-yl]methanol

Product 1

HCID 10288768[5-Methoxy-2-methyl-4-(3-methyl-4'-trifluoromethyl-biphenyl-4-ylmethylsulfanyl)-phenoxy]-acetic acid

Procedure

Preparation of (3-Methyl-4′-trifluoromethyl-biphenyl-4-yl)-methanol (compound 39A) The title compound was prepared in the manner analogous to Example 3A using (4-bromo-2-methyl-phenyl)-methanol and 4-(trifluoromethyl)benzeneboronic acid. MS m/z 249 (M-OH). Step 2. Preparation of 4chloromethyl-3-methyl-4′-trifluoromethyl-biphenyl (compound 39B) The title compound was prepared in the manner analogous to Example 3B using 39A. 400 MHz 1H NMR (DMSO-d6) δ 7.84 (d, 2H, J=8.3 Hz), 7.76 (d, 2H, J=8.3 Hz), 7.57 (s, 1H), 7.48 (m, 2H), 4.80 (s, 2H), 2.41 (s, 3H). Step 3. Preparation of [5-Methoxy-2-methyl-4-(3-methyl-4′-trifluoromethyl-biphenyl-4-ylmethylsulfanyl)-phenoxy]-acetic acid methyl ester (compound 39C) The title compound was prepared in the manner analogous to Example 1F using 1D and 39B. MS m/z 491 (M+1). Step 4. Preparation of [5-Methoxy-2-methyl-4-(methyl-4′-trifluoromethyl-biphenyl-4-ylmethylsulfanyl)-phenoxy]-acetic acid (compound 39) The title compound was prepared in the manner analogous to Example 1 using 39C. IR cm−1: 1740, 1322; 400 MHz 1H NMR (DMSO-d6) δ 7.81 (d, 2H, J=8.1 Hz), 7.73 (d, 2H, J=8.1 Hz), 7.51 (s, 1H), 7.39 (d, 1H, J=7.8 Hz), 7.16 (d, 1H, J=7.8 Hz), 7.04 (s, 1H), 6.53 (s, 1H), 4.71 (s, 2H), 4.00 (s, 2H), 3.73 (s, 3H), 2.39 (s, 3H), 2.02 (s, 3H); MS m/z 477 (M+1). Anal. Calc'd for C25H23F3O4S.0.1 H2O; C, 62.78; H, 4.89; found: C, 62.57; H, 4.82.

Workup

  1. customwas prepared in the manner analogous to Example 3B

Sources & evidence

ORD record
ord-2fc7765219cd47b3b6cc2ad464b98c40
Source dataset
uspto-grants-2007_11
Patent number
USRE039916E1

Reaction notes

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