Iodoethane → 4-Bromo-2-ethyl-1-fluorobenzene

Temperature

100 °C

Ethyl iodide (0.14 ml, 1.8 mmol) was added to a solution of (5-bromo-2-fluorophenyl)(iodo)zinc (0.5M in tetrahydrofuran) (5.4 ml, 2.7 mmol) in HMPA (10 ml). The reaction mixture was heated to 100° C. for 48 hrs. After which time the reaction mixture was cooled to room temperature and partitioned between ethyl acetate (100 ml) and water (100 ml). The organic layer was separated and dried over anhydrous sodium sulfate, filtered and the solvent was removed in vacuo. The crude oil was purified by column chromatography on silica gel eluting with 80:20 hexanes:ethyl acetate, to afford the title compound as a yellow oil (0.4 g).

1. temperatureAfter which time the reaction mixture was cooled to room temperature
2. custompartitioned between ethyl acetate (100 ml) and water (100 ml)
3. customThe organic layer was separated
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. customthe solvent was removed in vacuo
7. customThe crude oil was purified by column chromatography on silica gel eluting with 80:20 hexanes

ORD record

ord-86c3f171c51c4db394d1041ae72e6178

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07473790B2