Sodium Hydroxide → 1-(Chloromethyl)-3-iodobenzene
Reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]O.S(Cl)([Cl:12])=O.[OH-].[Na+]>C(Cl)Cl.O>[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][Cl:12]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 3-iodobenzyl alcohol (600 mg, 2.56 mmol) in DCM (3 ml) was treated with thionyl chloride (3 ml, 41.3 mmol) and stirred at ambient temperature for 18 h, before addition of further thionyl chloride (1 ml, 13.7 mmol) and heating to reflux for 12 h. The cooled solution was basified with 50% NaOH, diluted with water and extracted with DCM. The combined organics were dried over MgSO4, filtered and evaporated to afford a clear syrup which crystallises on standing to give 3-iodobenzyl chloride as a white solid (650 mg, quant.).
Workup
- temperatureheating
- temperatureto reflux for 12 h
- extractionextracted with DCM
- dry with materialThe combined organics were dried over MgSO4
- filtrationfiltered
- customevaporated
- customto afford a clear syrup which
- customcrystallises
Sources & evidence
- ORD record
- ord-3acf1a00cf5945cdbaecb6b59e93182f
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962665B2
Reaction notes
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