3-Methyl-4-[2-(trifluoromethyl)phenyl]benzoic acid → 3-Methoxy-4-(4-methyl-3-thienyl)benzoic acid

HRID 219779Notes

Reaction equation

HRID 219779 reaction equation
CC1C=C(C(O)=O)C=CC=1C1C=CC=CC=1C(F)(F)F.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:30]=[CH:31][C:32]=1[C:33]1[C:37]([CH3:38])=[CH:36][S:35][CH:34]=1)[C:26]([O:28]C)=[O:27]>>[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:30]=[CH:31][C:32]=1[C:33]1[C:37]([CH3:38])=[CH:36][S:35][CH:34]=1)[C:26]([OH:28])=[O:27]

Participants

3

Reactant 2

HCID 219478123-Methyl-4-[2-(trifluoromethyl)phenyl]benzoic acidHCID 67400074Methyl 3-methoxy-4-(4-methyl-3-thienyl)benzoate

Product 1

HCID 594957953-Methoxy-4-(4-methyl-3-thienyl)benzoic acidYield 83.1%

Procedure

The title compound was prepared following procedure described for Intermediate 5, step 2, but starting from methyl 3-methoxy-4-(4-methyl-3-thienyl)benzoate (2.30 g; 8.77 mmol; 1 eq.), affording the title compound as a brown solid (1.81 g, 83%). 1H NMR: (DMSO-d6, 300 MHz) δ 13.05 (s, 1H), 7.62-7.59 (m, 2H), 7.40-7.39 (d, J=3.23 Hz, 1H), 7.32-7.29 (d, J=7.48 Hz, 1H), 7.25-7.23 (m, 1H), 3.82 (s, 3H), 2.99 (s, 3H). LC/MS (Method A): 248.8 (M+H)+; 246.9 (M−H)−. HPLC (Method A) Rt 3.99 min (Purity: 97.4%).

Workup

  1. customThe title compound was prepared following procedure

Sources & evidence

ORD record
ord-ea53f75f7fbe4e24bff58f84368d31af
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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