Iodoethane → 2-Bromophenetole
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].I[CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:10][CH3:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Into a 500-mL round-bottom flask was placed CH3COCH3 (200 mL), 2-bromophenol (10.38 g, 60.00 mmol, 1.00 equiv), iodoethane (28.08 g, 180.04 mmol, 3.00 equiv) and potassium carbonate (33.12 g, 239.64 mmol, 3.99 equiv). The resulting solution was heated to reflux overnight in an oil bath. The solids were filtered out. The filtrate was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:100). Purification afforded 11.48 g (95%) of 1-bromo-2-ethoxybenzene as a colorless oil.
Workup
- customInto a 500-mL round-bottom flask was placed
- temperatureThe resulting solution was heated
- temperatureto reflux overnight in an oil bath
- filtrationThe solids were filtered out
- concentrationThe filtrate was concentrated under vacuum
- customPurification
Sources & evidence
- ORD record
- ord-c41bb86b516b4a38ad60daf8e2dc2224
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969557B2
Reaction notes
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