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

HRID 1628195Notes

Reaction equation

HRID 1628195 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]([CH2:20][C:21]([O:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)=[O:22])[CH:15]=1.CC(O)=O.C(Cl)Cl>CCCCCCC.CCOC(C)=O.[Zn]>[F:34][C:32]([F:33])([F:35])[C:29]1[CH:28]=[CH:27][C:26]([CH2:25][CH2:24][O:23][C:21]([CH2:20][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)=[O:22])=[CH:31][CH:30]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 866503122-{3-[2-(4-Trifluoromethyl-phenyl)-ethoxycarbonylmethyl]phenylsulfanylmethyl}-benzoic acid 2,2,2-trichloro-ethyl ester

Product 1

HCID 581194622-{3-[2-(4-Trifluoromethyl-phenyl)-ethoxycarbonylmethyl]-phenylsulfanylmethyl}-benzoic acidYield 69.5%

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-[2-(4-trifluoromethyl-phenyl)-ethoxycarbonylmethyl]phenylsulfanylmethyl}-benzoic acid 2,2,2-trichloro-ethyl ester (160 mg, 0.264 mmol), zinc (345 mg, 5.28 mmol), HOAc, 97% (1.51 mL, 26.4 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 (87 mg, 69%) as an oil; 1H NMR (400 MHz, CDCl3): δ 2.97 (dd, 2H), 3.54 (s, 2H), 4.34 (dd, 2H), 4.58 (s, 2H), 7.00-7.06 (m, 1H), 7.12-7.18 (m, 2H), 7.21-7.34 (m, 5H), 7.42 (dd, 1H), 7.52 (d, 2H), 7.98 (d, 1H); Mass spectrum: M−H+ 473.

Workup

  1. customThe titled compound was prepared

Sources & evidence

ORD record
ord-2d3c88b809904609a94ffa84ceffe661
Source dataset
uspto-grants-2014_07
Patent number
US08785681B2

Reaction notes

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