Acetic Acid → 2-{4-[2-(4-Trifluoromethyl-phenyl)-acetoxymethyl]-phenylsulfanylmethyl}-benzoic acid

HRID 709507Notes

Reaction equation

HRID 709507 reaction equation
ClC(Cl)(Cl)C[O:4][C:5](=[O:35])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][O:21][C:22](=[O:34])[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)=[CH:16][CH:15]=1.CC(O)=O.C(Cl)Cl>CCCCCCC.CCOC(C)=O.[Zn]>[F:33][C:30]([F:31])([F:32])[C:27]1[CH:26]=[CH:25][C:24]([CH2:23][C:22]([O:21][CH2:20][C:17]2[CH:18]=[CH:19][C:14]([S:13][CH2:12][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[C:5]([OH:35])=[O:4])=[CH:15][CH:16]=2)=[O:34])=[CH:29][CH:28]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 866503092-{4-[2-(4-Trifluoromethyl-phenyl)-acetoxymethyl]phenylsulfanylmethyl}benzoic acid 2,2,2-trichloro-ethyl ester

Product 1

HCID 581194702-{4-[2-(4-Trifluoromethyl-phenyl)-acetoxymethyl]-phenylsulfanylmethyl}-benzoic acidYield 69%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Procedure

The titled compound was prepared according to the method described for example 1 above from 2-{4-[2-(4-trifluoromethyl-phenyl)-acetoxymethyl]phenylsulfanylmethyl}benzoic acid 2,2,2-trichloro-ethyl ester (112 mg, 0.189 mmol), zinc (247 mg, 3.79 mmol), HOAc, 97% (1.08 mL, 18.9 mmol) and DCM (9 mL). The crude was submitted to flash chromatography using heptane and EtOAc (70/30-60/40) as eluent to give the titled compound (60 mg, 69%) as a solid; 1H NMR (400 MHz, CDCl3): δ 3.72 (s, 2H), 4.57 (s, 2H), 5.09 (s, 2H), 7.18 (d, 2H), 7.24-7.30 (m, 3H), 7.31-7.46 (m, 4H), 7.48 (d, 2H), 8.05 (d, 1H); Mass spectrum: M−H+ 459.

Workup

  1. customThe titled compound was prepared

Sources & evidence

ORD record
ord-11ca173e6f264c02b6aeb47ed5876d5c
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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