5-Bromo-2-ethoxybenzaldehyde → HCID 12542423, compound

HRID 1821038Notes

Reaction equation

[CH3:1]C(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:16][CH2:17][CH3:18])=[C:12]([CH:15]=1)[CH:13]=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.CCOCC>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:16][CH2:17][CH3:18])=[C:12]([CH:15]=1)[CH:13]=[CH2:1]

Participants

Conditions

Temperature: -78 °C

Procedure

Methyltriphenylphosphonium bromide (1.09 g, 3.05 mmol) was added to a solution of potassium t-butoxide (0.5 g, 2.29 mmol) in THF (8 mL). The resulting reaction mixture turned bright yellow and was stirred for 40 min after which, it was cooled to −78° C. 5-bromo-2-ethoxybenzaldehyde was dissolved in THF (2 mL) and added to the reaction which was stirred for 2 h. The reaction was warmed to rt, diluted with ether and filtered through celite. The filtrate was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography eluting with 15% EtOAc/hexanes yielded 320 mg of the desired product: 1H NMR (500 MHZ, CDCl3) δ 7.58 (d, J=2.5 Hz, 1H), 7.31 (dd, J=6.4, 2.4 Hz, 1H), 6.96-7.04 (m, 1H), 6.74 (d, J=8.7 Hz, 1H), 5.77 (d, 1H), 5.32 (d, 1H), 4.03-4.07 (m, 2H), 1.45 (t, J=7.0 Hz, 3H).

Workup

customThe resulting reaction mixture
additionadded to the reaction which
stirringwas stirred for 2 h
temperatureThe reaction was warmed to rt
filtrationfiltered through celite
washThe filtrate was washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
washSilica gel chromatography eluting with 15% EtOAc/hexanes

Sources & evidence

ORD record: ord-fca38f11f73941e58596b5caed8199bc
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605171B2

Reaction notes

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