Water → 1-Bromo-4-(propan-2-yloxy)benzene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH:16]([CH3:18])[CH3:17].O>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:16]([CH3:18])[CH3:17])=[CH:4][CH:3]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 4-bromophenol (16-2, 7.02 g, 39.4 mmol) and potassium carbonate (12.6 g, 90.9 mmol) in DMSO (20.0 mL) was added with 2-iodopropane (16-1, 5.2 mL, 49.0 mmol). The mixture was heated at 60° C. overnight. The solution was cooled to room temperature and added with water (200 mL). The reaction was extracted with EtOAc, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (EtOAc:hexanes=1:100 as eluant) to give 1-bromo-4-isopropoxybenzene (6.66 g) as colorless oil in 79% yield: 1H NMR (CDCl3) δ 7.34 (m, 2 H), 6.77 (dd, J=8.9, 3.1 Hz, 2 H), 4.49 (m, 1 H), 1.33 (s, 3 H), 1.31 (m, 3 H).
Workup
- temperatureThe solution was cooled to room temperature
- extractionThe reaction was extracted with EtOAc
- dry with materialdried over MgSO4
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash column chromatography on silica gel (EtOAc:hexanes=1:100 as eluant)
Sources & evidence
- ORD record
- ord-27fddfb7d01e40ebbcb0907fdd7ef6de
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999983B2
Reaction notes
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