1,2-Dibromoethane → 2-Bromo-1-(2-bromoethoxy)-4-methylbenzene
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[Br:10][CH2:11][CH2:12]Br.[OH-].[Na+]>O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:12][CH2:11][Br:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 2-bromo-4-methylphenol (5.0 g, 26 mmol), 1,2-dibromoethane (7.0 g, 37 mmol) in water (20 mL) and NaOH (1.1 g, 28 mmol) was stirred at 100° C. for 24 h. The mixture was extracted with DCM (150 mL), washed with water, brine, dried and concentrated. The residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (20:1) to give the title compound (1a).
Workup
- extractionThe mixture was extracted with DCM (150 mL)
- washwashed with water, brine
- customdried
- concentrationconcentrated
- customThe residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (20:1)
Sources & evidence
- ORD record
- ord-49cdafceecf241adbafd1dc3d1079e92
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206166B2
Reaction notes
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