Ethanolamine → 2-[(4-Bromo-3-methylphenyl)amino]ethan-1-ol
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[CH3:9].[NH2:10][CH2:11][CH2:12][OH:13].N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.CCOC(C)=O.[Cu]I>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:10][CH2:11][CH2:12][OH:13])=[CH:4][C:3]=1[CH3:9]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 2-bromo-5-iodotoluene (1.60 g, 5.40 mmol), 2-aminoethanol (0.49 mL, 8.14 mmol), CuI (53.3 mg, 0.28 mmol), L-proline (63.4 mg, 0.55 mmol) and K2CO3 (1.49 g, 10.8 mmol) in DMSO (3.24 mL) was stirred at 60° C. for 12 hours. The reaction mixture was cooled and then diluted with AcOEt, and the organic layer was sequentially washed with H2O and saturated brine. The organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/AcOEt=1/1) to give 2-(4-bromo-3-methyl-phenylamino)-ethanol as a brown solid (1.00 g, 81%).
Workup
- temperatureThe reaction mixture was cooled
- washthe organic layer was sequentially washed with H2O and saturated brine
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (hexane/AcOEt=1/1)
Sources & evidence
- ORD record
- ord-13de300069af41e199aa40862afcac30
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09169254B2
Reaction notes
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