Methyl iodide → 2-Bromo-4-tert-butyl-1-methoxybenzene
Reaction equation
IC.BrC1C=C(C(C)(C)C)C=CC=1O.[Br:15][C:16]1[C:25]2[O:24][CH2:23]N(C(C)(C)C)C[C:20]=2[CH:19]=[C:18]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:15][C:16]1[CH:17]=[C:18]([C:30]([CH3:31])([CH3:33])[CH3:32])[CH:19]=[CH:20][C:25]=1[O:24][CH3:23]Participants
6
Procedure
Iodomethane (10.0 mL, 0.161 mol) was added to a mixture of 2-bromo-4-(tert-butyl)phenol [Intermediate 1, Step 1] (29.5 g, 0.129 mol) and potassium carbonate (42.7 g, 0.309 mol) in dry acetone (400 mL) and the reaction mixture refluxed under nitrogen for 22 hours. The cooled reaction mixture was then concentrated and the residue partitioned between ethyl acetate (400 mL) and 0.3 M aqueous sodium hydroxide solution (300 mL). The organic phase was separated, washed with water (300 mL) and saturated brine (300 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give 2-bromo-4-(tert-butyl)-1-methoxybenzene (32.09 g, 100% yield) as a light yellow oil.
Workup
- temperaturethe reaction mixture refluxed under nitrogen for 22 hours
- customThe cooled reaction mixture
- concentrationwas then concentrated
- customthe residue partitioned between ethyl acetate (400 mL) and 0.3 M aqueous sodium hydroxide solution (300 mL)
- customThe organic phase was separated
- washwashed with water (300 mL) and saturated brine (300 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5503d8bd2ae44dc89fa7c8de199290e2
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962657B2
Reaction notes
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