Iodine → HCID 18788666, compound

Temperature

22 °C

A stirred solution of 3.00 g (15.5 mmol) of 1,4-dimethoxy-2-t-butylbenzene (obtained by methylation of t-butyl hydroquinone with sodium hydride and methyl iodide in tetrahydrofuran) and 2.52 g (21.7 mmol) of tetramethylethylenediamine in 50 mL of anhydrous ether under nitrogen is cooled to 0° C. and 8.66 mL (21.7 mmol) of n-butyllithium (2.5M in hexane) is added over a 5 minute period. The mixture is warmed to 22° C., stirred for 18 hours and then cooled back to 0° C. The reaction is quenched with 7.86 g (30.9 mmol) of iodine in 30 mL of tetrahydrofuran and partitioned between ethyl acetate (200 mL) and 10% NaHSO3 (300 mL). The organic layer is washed with water (50 mL), brine (50 mL), dried (MgSO4) and evaporated to give a brown, partially crystalline oil which is chromatographed on silica gel (eluting with 98:2 hexane/ethyl acetate) to give crude product which is recrystallized from hexane to obtain 2,5-dimethoxy-4-t-butylphenyl iodide (mp 80.5°-82.5° C.)

1. temperaturecooled back to 0° C
2. custompartitioned between ethyl acetate (200 mL) and 10% NaHSO3 (300 mL)
3. washThe organic layer is washed with water (50 mL), brine (50 mL)
4. dry with materialdried (MgSO4)
5. customevaporated
6. customto give a brown, partially crystalline oil which
7. customis chromatographed on silica gel (eluting with 98:2 hexane/ethyl acetate)
8. customto give crude product which
9. customis recrystallized from hexane

ORD record

ord-089db4943a244fb2a5db2cff82eae78b

Source dataset

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05656643