1,3-Dibromopropane → 5-(3-Bromopropoxy)benzo[d]thiazole
Reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([OH:10])=[CH:9][C:4]=2[N:3]=[CH:2]1.[Br:11][CH2:12][CH2:13][CH2:14]Br.C([O-])([O-])=O.[K+].[K+]>CCO>[Br:11][CH2:12][CH2:13][CH2:14][O:10][C:8]1[CH:7]=[CH:6][C:5]2[S:1][CH:2]=[N:3][C:4]=2[CH:9]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of intermediate 25 (1 g, 6.6 mmol), 1,3-dibromopropane (1.83 mL, 18 mmol), anhydrous K2CO3 (828 mg, 6.0 mmol) and EtOH (20 mL) was heated to reflux and stirred overnight. The yellow solid was filtered and purified by column chromatography (elution with PE/EtOAc=3:1) to afford 5-(3-bromopropoxy)benzo[d]thiazole (intermediate 27) (543 mg, 33%) as a yellow oil.
Workup
- temperaturewas heated
- temperatureto reflux
- filtrationThe yellow solid was filtered
- custompurified by column chromatography (elution with PE/EtOAc=3:1)
Sources & evidence
- ORD record
- ord-87fab5765c9e4b60bdfa7972a25b0bb7
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156822B2
Reaction notes
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