O-Cresol → 1-Iodo-2-[(2-methylphenoxy)methyl]benzene
Reaction equation
[H-].[Na+].[C:3]1([CH3:10])[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[I:19]>O1CCCC1>[I:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][O:9][C:8]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Sodium hydride (60% oil dispersion) (7.8 g) was added portionwise to a ice-water cooled solution of o-cresol (21.1 g) in tetrahydrofuran (500 mL). The mixture was stirred 20 minutes and then 1-(bromomethyl)-2-iodobenzene (58 g) was added. The mixture was warmed to 60° C. for 16 h. Additional sodium hydride (2 g) was added and the reaction mixture heated for an additional 3 h. The reaction mixture was cooled and carefully quenched with water and extracted with ethyl acetate (2×250 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure to an oil, which was triturated with cold hexane to provide a solid which was collected by filtration to yield 59.1 g (94%) of the title compound of Step B as a white solid, mp 106-108° C.
Workup
- temperaturethe reaction mixture heated for an additional 3 h
- temperatureThe reaction mixture was cooled
- customcarefully quenched with water
- extractionextracted with ethyl acetate (2×250 mL)
- dry with materialThe combined organic extracts were dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure to an oil, which
- customwas triturated with cold hexane
- customto provide a solid which
- filtrationwas collected by filtration
Sources & evidence
- ORD record
- ord-05e04f26e13443a5b8b8da93c1b73283
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05977149
Reaction notes
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