Water → 1-(2-Bromoethoxy)-4-iodobenzene
Reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Br:15][CH2:16][CH2:17]Br.O>CN(C=O)C>[Br:15][CH2:16][CH2:17][O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a stirring solution of 4-iodophenol (25 g, 110 mmol) and K2CO3 (31 g, 220 mmol) in DMF (250 mL) was added 1,2-dibromoethane (5 mL, 55 mmol) over a period of 1 hr. The solution was heated at 50° C. and stirred overnight under Ar. In order to complete the reaction additional reagents were added: 1,2-dibromoethane (20 mL, 220 mmol) and K2CO3 (6 g, 43 mmol) and the mixture was heated at 50° C. an additional 12 hours under Ar. Water was added and the reaction mixture was extracted with dichloromethane, dried over Na2SO4, filtered and the solvent evaporated under reduced pressure. The crude mixture was purified by silica gel chromatography eluted with 10% ethyl acetate in hexanes to give the title compound as a white solid (5.5 g, 17 mmol).
Workup
- additionwere added
- extractionthe reaction mixture was extracted with dichloromethane
- dry with materialdried over Na2SO4
- filtrationfiltered
- customthe solvent evaporated under reduced pressure
- customThe crude mixture was purified by silica gel chromatography
- washeluted with 10% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-b12707aff86546419767eb6a59514ec2
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06686502B1
Reaction notes
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