2-Bromo-5-(trifluoromethyl)benzaldehyde → 1-(2-Bromo-5-(trifluoromethyl)phenyl)ethanol

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Reaktionsgleichung

[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:14][Mg]Cl>C1COCC1.O>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:6][C:3]=1[CH:4]([OH:5])[CH3:14]

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

To a solution of 2-bromo-5-(trifluoromethyl)benzaldehyde (10 g, 39.6 mmol) in THF (40 mL), methyl magnesium chloride (3 M in THF) (26.4 mL, 79.3 mmol) was added at −78° C. dropwise. The reaction was warmed to 25° C. and stirred at this temperature for 1 h under a nitrogen atmosphere. Then the reaction mixture was diluted with water (200 mL) extracted with ethyl acetate (2×200 mL). Organic part was dried over sodium sulfate, filtered and concentrated in vacuum to give the crude compound which was further purified by column chromatography using silica gel (100 to 200 mesh) eluting with 0% to 10% ethyl acetate in hexanes to afford 1-(2-bromo-5-(trifluoromethyl)phenyl)ethanol (10.4 g, 98%) as a clear liquid. MS (ESI, Negative ion) m/z (M−1): 267.0. 1H NMR (400 MHz, DMSO) δ 7.87 (s, 1H), 7.80 (d, J=8.2 Hz, 1H), 7.55 (d, J=8.0 Hz, 1H), 5.68 (d, J=4.2 Hz, 1H), 5.03-4.94 (m, 1H), 1.32 (d, J=6.3 Hz, 3H).

Aufarbeitung

extractionextracted with ethyl acetate (2×200 mL)
dry with materialOrganic part was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuum
customto give the crude compound which
customwas further purified by column chromatography
washeluting with 0% to 10% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag: ord-1f6f4121210a4af6b0e608009c920879
Quelldatensatz: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09012443B2

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