Ethyl vinyl ether → 1-Bromo-2-[(1-ethoxyethoxy)methyl]-4-methoxybenzene

HRID 916866Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][OH:11].[CH:12]([O:14][CH2:15][CH3:16])=[CH2:13].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][O:11][CH:12]([O:14][CH2:15][CH3:16])[CH3:13]

Participants

Conditions

Temperature: 0 °C

Procedure

Dissolve (2-bromo-5-methoxy-phenyl)methanol (5.0 g, 23 mmol) in dry dichloromethane (120 mL) and cool to 0° C. under nitrogen. Add ethyl vinyl ether (2.5 g, 34 mmol) followed by pyridinium p-toluenesulfonate (580 mg, 2.3 mmol). Warm to room temperature and stir for 2 hours. Pour reaction into saturated aqueous sodium bicarbonate and extract twice with dichloromethane. Combine organic layers and wash with water and brine. Dry with sodium sulfate, filter and concentrate in vacuo to yield 6.6 g (100%) of title compound as a clear colorless oil. 1H NMR (CDCl3) δ 7.41 (d, J=8.6 Hz, 1H), 7.08 (d, J=3.1 Hz, 1H), 6.71 (dd, J=8.8, 3.1 Hz, 1H), 4.88 (q, J=5.3 Hz, 1H), 4.65 (ab, Jab=13.3 Hz, H), 4.55 (ab, Jab=13.3 Hz, 1H), 3.8 (s, 3H), 3.71 (m, 1H), 3.55 (m, 1H), 1.41 (d, J=5.3 Hz, 3H), 1.23 (t, J=7.0 Hz, 3H).

Workup

temperatureWarm to room temperature
additionPour
extractionextract twice with dichloromethane
washCombine organic layers and wash with water and brine
dry with materialDry with sodium sulfate
filtrationfilter
concentrationconcentrate in vacuo

Sources & evidence

ORD record: ord-250ce59c5bdb40808cd2707d44e78dc6
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271264B2

Reaction notes

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