Bromide ion → HCID 20766033, compound

HRID 860582Notes

Reaction equation

HRID 860582 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:14]([O:16][C:17]([C:19]1[S:23][C:22]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)=[N:21][C:20]=1[CH2:34]Br)=[O:18])[CH3:15].[Br-]>C(#N)C>[CH2:14]([O:16][C:17]([C:19]1[S:23][C:22]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:26][CH:25]=2)=[N:21][C:20]=1[CH2:34][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:18])[CH3:15]

Participants

6

Reactant 4

HCID 259Bromide ionHCID 996PhenolHCID 10796Cesium carbonateHCID 179517684-Bromomethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic Acid Ethyl Ester

Product 1

HCID 20766033HCID 20766033, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Phenol (0.518 g, 5.5 mmol) is combined with anhydrous acetonitrile (20 mL) and cesium carbonate (2.3 g, 10 mmol) and allowed to stir at room temperature under nitrogen. To the reaction is added 4-bromomethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester (1.97 g, 5.00 mmol). The reaction is monitored by TLC until all of the bromide is consumed. The reaction is diluted with ethyl ether (100 mL), then 0.1N NaOH (50 mL) is added. The two phases are separated, then the organic layer is washed with water (50 mL) and brine (50 mL). The organic layer is dried over anhydrous sodium sulfate, then concentrated. The material is further purified using flash chromatography to yield 1.75 g or 86% yield of the product.

Workup

  1. customis consumed
  2. additionThe reaction is diluted with ethyl ether (100 mL)
  3. addition0.1N NaOH (50 mL) is added
  4. customThe two phases are separated
  5. washthe organic layer is washed with water (50 mL) and brine (50 mL)
  6. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe material is further purified

Sources & evidence

ORD record
ord-f86bffd45f17450f91ccf3d15acc66eb
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

Loading…