Iodine → 5-Bromo-2,2-dimethyl-2,3-dihydro-1-benzofuran

To a solution of 4-bromo-2-(2-methylallyl)phenol (7) (4.5 g, 19.8 mmol) in CH2Cl2 (250 mL) was added iodine (1.3 g, 4.95 mmol) and the mixture stirred at room temperature for 48 h. The mixture was then diluted with methyl tert-butyl ether (100 mL) and washed with H2O (50 mL), brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, eluting with 5% ethyl acetate in hexanes) to give the title compound (8) (4.0 g, 88%) as yellow liquid. 1H NMR (CDCl3, 400 MHz) δ 7.24 (s, 1H), 7.20 (d, J=8.4 Hz, 1H), 6.61 (d, J=8.4 Hz, 1H), 3.00 (s, 2H), 1.47 (s, 6H); MS (ESI, M+H+) C10H12BrO, calcd. 227.1. found 227.0, 229.0.

1. washwashed with H2O (50 mL), brine (50 mL)
2. dry with materialdried over anhydrous sodium sulfate
3. concentrationconcentrated under reduced pressure
4. customThe residue was purified by flash chromatography (silica gel, eluting with 5% ethyl acetate in hexanes)

ORD record

ord-2b90285366544913aa61d40ffbd08321

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08334292B1