1-Bromo-4-iodobenzene → Benzene, 1-bromo-4-ethynyl-

To a solution of zinc bromide (9.0 g, 40 mmol) in anhydrous THF (100 mL) at room temperature under a nitrogen atmosphere was added a solution of ethynyl magnesium bromide (0.5 M in THF, 60 mL, 30 mmol). After 5 minutes 4-bromo-iodobenzene was added (5.64 g, 20 mmol) followed by tetrakis triphenyl phosphine palladium (0) (1.15 g, 1.0 mmol). The reaction was stirred at room temperature for 18 hours. The reaction mixture was poured into brine and extracted with ether (4×100 mL). The ether layer was washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography with hexanes to give the title compound as a yellow solid. 1H NMR (CDCl3, 500 MHz): δ 7.51(d, J=8.5 Hz, 2H), 7.4(d, J=8.5 Hz, 1H), 3.16(s, 1H).

1. extractionextracted with ether (4×100 mL)
2. washThe ether layer was washed with brine
3. dry with materialdried over anhydrous MgSO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe residue was purified by flash chromatography with hexanes

ORD record

ord-5c67594f62a7449dbd7a4f3a05e115c0

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07572922B2