Methyl iodide → 1-Bromo-4-(methoxymethyl)benzene
Reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[CH3:14]I>CN(C)C=O.O>[CH3:14][O:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1Participants
Procedure
4-Bromobenzyl alcohol (1.87 g) was added over 10 minutes to a stirred suspension of sodium hydride (0.24 g - used directly in the form of 0.48 g of a 50% dispersion in oil) in dry N,N-dimethylformamide (10 cm3) under an atmosphere of nitrogen. Afer evolution of hydrogen had ceased (20 minutes), methyl iodide (1.42 g) was added and the reaction mixture was stirred for a further 10 minutes. The mixture was poured into water and the organic layer separated. The aqueous layer was extracted with diethyl ether. The combined organic layers were dried over anhydrous sodium sulphate, and concentrated by evaporation under reduced pressure. The residual, crude product was purified by column chromatography on a silica gel support, eluting with n-hexane containing 12.5% by volume ethyl acetate, to give 4-bromobenzyl methyl ether (1.6 g).
Workup
- additionwas added
- customthe organic layer separated
- extractionThe aqueous layer was extracted with diethyl ether
- dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
- concentrationconcentrated by evaporation under reduced pressure
- customThe residual, crude product was purified by column chromatography on a silica gel support
- washeluting with n-hexane containing 12.5% by volume ethyl acetate
Sources & evidence
- ORD record
- ord-277c3836187a4589b55364d30ccdaeb5
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05196610
Reaction notes
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