Acetic Acid → 2-[4-(4-Trifluoromethyl-benzyloxycarbonylmethyl)-phenylsulfanylmethyl]-benzoic acid

HRID 709508Notes

Reaction equation

HRID 709508 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][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[O:22])=[CH:16][CH:15]=1.CC(O)=O.C(Cl)Cl>CCCCCCC.CCOC(C)=O.[Zn]>[F:34][C:31]([F:32])([F:33])[C:28]1[CH:29]=[CH:30][C:25]([CH2:24][O:23][C:21]([CH2:20][C:17]2[CH:16]=[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:35])=[O:4])=[CH:19][CH:18]=2)=[O:22])=[CH:26][CH:27]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 866503102-[4-(4-Trifluoromethyl-benzyloxycarbonylmethyl)phenylsulfanylmethyl]-benzoic acid 2,2,2-trichloro-ethyl ester

Product 1

HCID 581194682-[4-(4-Trifluoromethyl-benzyloxycarbonylmethyl)-phenylsulfanylmethyl]-benzoic acidYield 63%

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-(4-trifluoromethyl-benzyloxycarbonylmethyl)phenylsulfanylmethyl]-benzoic acid 2,2,2-trichloro-ethyl ester (74 mg, 0.125 mmol), zinc (164 mg, 2.50 mmol), HOAc, 97% (0.72 mL, 12.5 mmol) and DCM (5 mL). The crude was submitted to flash chromatography using heptane and EtOAc (70/30-60/40) as eluent to give the titled compound (36 mg, 63%) as a solid; 1H NMR (400 MHz, CDCl3): δ 3.64 (s, 2H), 4.54 (s, 2H), 5.18 (s, 2H), 7.16 (d, 2H), 7.23-7.29 (m, 3H), 7.29-7.35 (m, 3H), 7.37-7.43 (m, 3H), 7.60 (d, 2H), 8.03 (d, 1H); Mass spectrum: M−H+ 459.

Workup

  1. customThe titled compound was prepared

Sources & evidence

ORD record
ord-f53448db472e4321afe01205c503cb2c
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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