Chloroiodomethane → 1-Bromo-4-cyclopropoxybenzene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]=[CH2:10])=[CH:4][CH:3]=1.Cl[CH2:12]I.C([Zn]CC)C>ClC(Cl)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:12][CH2:10]2)=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
39.0 g (176 mmol) 1-Bromo-4-vinyloxybenzene and 32.4 mL (441 mmol) chloroiodomethane are added to 500 mL dichloroethane and cooled to 0° C. During 1 h 200 mL (200 mmol) diethylzinc solution (c=1 mol/l in hexane) are added and stirring is continued for 2 h at 0° C. The reaction is quenched by the addition of 200 mL of a sat. aq. NH4Cl solution and extracted with TBME (2×). The organic phases are combined, washed with brine, dried over MgSO4 and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, PE).
Workup
- customThe reaction is quenched by the addition of 200 mL of a sat. aq. NH4Cl solution
- extractionextracted with TBME (2×)
- washwashed with brine
- dry with materialdried over MgSO4
- customthe solvent is removed in vacuo
- customThe crude product is purified by column chromatography (silica gel, PE)
Sources & evidence
- ORD record
- ord-0821604af10a42ccbd7d699a7898a68e
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759528B2
Reaction notes
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