Benzaldehyde → HCID 16735193, compound

HRID 2252394Notes

Reaction equation

[CH:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.C([Li])CCC.[CH:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[O:7]([C:8]1[CH:13]=[CH:12][C:11]([CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[OH:27])=[CH:10][CH:9]=1)[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of 4-bromodiphenyl ether (2.0 g, 8.03 mmol) in THF (15 mL) at −78° C. was added n-butyllithium (3.85 mL, 2.6 M solution in hexanes). The reaction was stirred under argon for 2 hrs before a solution of benzaldehyde (0.85 g, 8.03 mmol) in THF at −78° C. was added. After stirring at −78° C. for 2 hrs, the reaction was quenched with water and extracted with ether. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give the crude product. The crude mixture was purified via flash SiO2 chromatography (ethyl acetate/hexanes (10%/90%) to (15%/85%)) to give 127 (2.22 g, 97% yield): 1H-NMR (400 MHz, chloroform-d) δ 7.28-7.40 (m, 9 H), 7.10 (t, J=7.6, 1 H), 6.94-7.01 (m, 4 H), 5.84 (d, J=3.6 Hz, 1 H), 2.17 (d, J=3.6 Hz, 1 H).

Workup

additionwas added
customthe reaction was quenched with water
extractionextracted with ether
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give the crude product
customThe crude mixture was purified via flash SiO2 chromatography (ethyl acetate/hexanes (10%/90%) to (15%/85%))

Sources & evidence

ORD record: ord-8b464571a3c441dbab5935d700811a68
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07321065B2

Reaction notes

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