Thiophenol → (6-Methoxy-2'-phenylsulfanylmethyl-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

HRID 38687Notes

Reaction equation

HRID 38687 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24]Br)[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2].[C:27]1([SH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[H-].[Na+]>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24][S:33][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 67430388(2'-Bromomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

Product 1

HCID 67432230(6-Methoxy-2'-phenylsulfanylmethyl-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2′-bromomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (0.103 g, 0.24 mmol) and thiophenol (0.03 mL, 0.26 mmol) in 1,4-dioxane (2 mL) was added sodium hydride (60% in mineral oil; 0.013 g, 0.29 mmol), and the reaction was stirred for 30 minutes at room temperature. The mixture was partitioned between EtOAc and H2O, and the aqueous layer was acidified and extracted three times with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography to give the title compound.

Workup

  1. customThe mixture was partitioned between EtOAc and H2O
  2. extractionextracted three times with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-be16ad000b6448a4b2ba2df3691ede36
Source dataset
uspto-grants-2013_09
Patent number
US08524748B2

Reaction notes

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