Acetic Acid → 2-{3-[1-(4-Trifluoromethyl-phenyl)-ethoxycarbonylmethyl]phenylsulfanylmethyl}-benzoic acid

HRID 709509Notes

Reaction equation

HRID 709509 reaction equation
ClC(Cl)(Cl)C[O:4][C:5](=[O:36])[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][CH:17]=[C:16]([CH:20]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:15]=1.CC(O)=O.C(Cl)Cl>CCCCCCC.CCOC(C)=O.[Zn]>[F:30][C:27]([F:28])([F:29])[C:24]1[CH:23]=[CH:22][C:21]([CH:20]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:16]2[CH:15]=[C:14]([S:13][CH2:12][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[C:5]([OH:36])=[O:4])[CH:19]=[CH:18][CH:17]=2)=[CH:26][CH:25]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 866503112-{3-[1-(4-Trifluoromethyl-phenyl)-ethoxycarbonylmethyl]phenylsulfanylmethyl}-benzoic acid 2,2,2-trichloro-ethyl ester

Product 1

HCID 668652792-{3-[1-(4-Trifluoromethyl-phenyl)-ethoxycarbonylmethyl]phenylsulfanylmethyl}-benzoic acidYield 77%

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-{3-[1-(4-Trifluoromethyl-phenyl)-ethoxycarbonylmethyl]phenylsulfanylmethyl}-benzoic acid 2,2,2-trichloro-ethyl ester (157 mg, 0.0.259 mmol), zinc (339 mg, 5.18 mmol), HOAc, 97% (1.48 mL, 25.9 mmol) and DCM (12 mL). The crude was submitted to flash chromatography using heptane and EtOAc (70/30-60/40) as eluent to give the titled compound (94 mg, 77%) as an oil; 1H NMR (400 MHz, CDCl3): δ 1.53 (s, 3H), 3.60 (dd, 2H), 4.54 (dd, 2H), 5.91 (m, 1H), 7.07-7.12 (m, 1H), 7.15-7.20 (m, 2H), 7.21-7.32 (m, 3H), 7.35-7.42 (m, 3H), 7.58 (d, 2H), 7.98 (d, 1H); Mass spectrum: M−H+ 473.

Workup

  1. customThe titled compound was prepared

Sources & evidence

ORD record
ord-f3aa21c459aa43ff83d946586fe94674
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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