Bromine → HCID 131733924, compound

HRID 709839Notes

Reaction equation

HRID 709839 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[S:11][CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[N:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:25]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)(=O)C>[Br:25][C:12]1[S:11][C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])=[N:14][C:13]=1[C:15]1[CH:16]=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 131733925HCID 131733925, compound

Product 1

HCID 131733924HCID 131733924, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-((tert-butyldimethylsilyloxy)methyl)-4-(4-(trifluoromethyl)phenyl)thiazole (500 mg) in ethyl acetate (10 mL) was added bromine (428 mg), and the mixture was stirred at room temperature 12 hr, and further at 60° C. for 2 hr. To the reaction mixture was added aqueous sodium thiosulfate solution, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give a crude product of the title compound. This compound was used for the next step without further purification.

Workup

  1. waitfurther at 60° C. for 2 hr
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-75d9eebad69b4abaa79e8b9359e33844
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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