Sodium hydride → HCID 58372816, compound

HRID 888470Notes

Reaction equation

HRID 888470 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=2[CH2:24]Br)[CH:7]=1)[CH3:2].[F:27][C:28]([F:32])([F:31])[CH2:29][SH:30].[H-].[Na+]>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=2[CH2:24][S:30][CH2:29][C:28]([F:32])([F:31])[F:27])[CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 41339242,2,2-TrifluoroethanethiolHCID 58372748HCID 58372748, compound

Product 1

HCID 58372816HCID 58372816, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To [3-(2-bromomethyl-4-nitro-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester (2.0 g, 4.72 mmol) and 2,2,2-trifluoroethanethiol (0.46 mL, 5.18 mmol) in 1,4-dioxane (40 mL) at 0° C. was added sodium hydride (60% in mineral oil; 0.207 g, 5.18 mmol), and the reaction was stirred at 0° C. for 30 minutes. The mixture was partitioned between EtOAc and H2O. The aqueous layer was separated and acidified, and then extracted 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. customThe aqueous layer was separated
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7fe6601e4e0e47f28e53f59e4740ab7e
Source dataset
uspto-grants-2012_08
Patent number
US08247602B2

Reaction notes

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