1,2-Dichloroethane → 5-bromo-N,N-diethyl-2-hydroxybenzamide
Reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[Br:6][C:7]1[CH:15]=[C:11]([C:12]([OH:14])=O)[C:10]([OH:16])=[CH:9][CH:8]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([OH:16])=[C:11]([CH:15]=1)[C:12]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[O:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Diethylamine (2.39 mL, 23.0 mmol) was added to a solution of 5-bromosalicylic acid (1.000 g, 4.61 mmol), EDC (1.33 g, 6.91 mmol), HOAt (0.627 g, 4.61 mmol) and DMF (20.0 mL) and the system was flushed with argon. The tube was sealed and the mixture stirred at 50° C. for 12 h. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a brown oil. This oil was purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-50% ethyl acetate-hexane) to afford 5-bromo-N,N-diethyl-2-hydroxybenzamide as an off-white solid. MS m/z=272.1, 274.1 [M+H]+. Calcd for C11H14BrNO2: 272.1.
Workup
- customthe system was flushed with argon
- customThe tube was sealed
- customThe reaction mixture was partitioned between ethyl acetate and water
- customThe aqueous phase was separated
- extractionextracted with ethyl acetate
- washThe combined organic phases were washed with brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto afford a brown oil
- customThis oil was purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-50% ethyl acetate-hexane)
Sources & evidence
- ORD record
- ord-b18d29ca88ca4e7a9a4d179899743626
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426447B2
Reaction notes
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