Iodine → 1-Iodo-4-methoxy-2-(methoxymethoxy)benzene

HRID 521747Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH2:11][O:12][CH3:13].[Li]CCCC.[I:19]I>C1COCC1>[I:19][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH2:11][O:12][CH3:13]

Participants

Conditions

Temperature: 23 °C

Procedure

To a stirred solution of 2-bromo-5-methoxy-1-methoxymethoxybenzene (1.04 g, 4.23 mmol) in THF (13 mL) at −95° C. (hexanes/N2) was added n-BuLi (1.6 M in hexanes, 2.91 mL, 4.65 mmol) and the resulting solution was stirred for 5 min. To this solution was then added by syringe a solution of I2 (1.28 g, 5.07 mmol) in THF (8.5 mL) until a yellow color persisted. The solution was then permitted to warm to 23° C. and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, petroleum ether:Et2O 8:1) to provide 2-iodo-5-methoxy-1-methoxymethoxybenzene as a pale-orange oil (1.04 g, 84%). See also Tsukayama, M., 1997.

Workup

concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (SiO2, petroleum ether:Et2O 8:1)

Sources & evidence

ORD record: ord-1cc1e574176a4fcf8c277c2ba71d4f0b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328127B2

Reaction notes

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