Benzyl Bromide → 2-Phenyl-1-(thiazol-2-yl)ethanone
Reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([O:9][Si](C)(C)C)[C:7]#N.C(Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[C:15]1([CH2:7][C:6]([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)=[O:9])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of the product from Step 1 (0.4 g, 1.9 mmol) in degassed THF (4 mL) at −78° C. was added LHMDs. After stirring at −78° C. for 15 min, benzyl bromide (0.27 mL, 2.3 mmol) was added, and stirring was continued at −78° C. for 15 min, followed by 1 h at r.t. The reaction was then quenched by the addition of saturated NH4Cl solution, and the product was extracted with EtOAc. The organic layer was washed with H2O and brine, and was then dried (MgSO4), filtered, and evaporated. The residue was purified by flash chromatography (1:10 EtOAc:hexane) to give 0.16 g of the product.
Workup
- stirringstirring
- waitwas continued at −78° C. for 15 min
- waitfollowed by 1 h at r.t
- customThe reaction was then quenched by the addition of saturated NH4Cl solution
- extractionthe product was extracted with EtOAc
- washThe organic layer was washed with H2O and brine
- dry with materialwas then dried (MgSO4)
- filtrationfiltered
- customevaporated
- customThe residue was purified by flash chromatography (1:10 EtOAc:hexane)
Sources & evidence
- ORD record
- ord-082dd7de13a045569fc80662d61fcfd0
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06486142B2
Reaction notes
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