Water → 4-Bromo-5-(((tert-butyldimethylsilyl)oxy)methyl)thiazole
Reaction equation
Br[C:2]1[S:3][C:4]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[C:5]([Br:7])[N:6]=1.C([Li])CCC.O>C(OCC)C>[Br:7][C:5]1[N:6]=[CH:2][S:3][C:4]=1[CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:11])[CH3:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a −78° C. solution of 2,4-dibromo-5-{[(tert-butyldimethylsilyl)oxy]methyl}-1,3-thiazole (2.44 g, 6.3 mmol) in anhydrous diethyl ether (120 mL) was added a solution of n-butyl lithium (2.5M in hexanes, 2.5 mL, 6.3 mmol). The reaction mixture was stirred at −78° C. for 1 hour. Water (75 mL) was added, and the mixture was warmed to room temperature then extracted with EtOAc (3×75 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording 4-bromo-5-{[(tert-butyldimethylsilyl)oxy]methyl}-1,3-thiazole (1.77 g, 90%). The product was used without further purification.
Workup
- temperaturethe mixture was warmed to room temperature
- extractionthen extracted with EtOAc (3×75 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
- customdried in vacuo
Sources & evidence
- ORD record
- ord-79a9b46563184a00bef689eb35245d98
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040538B2
Reaction notes
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