Hydrochloric Acid → 4-[1-(3-Bromo-phenyl)-vinyl]-phenol

HRID 1668710Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=1.O1CCCCC1[O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=O)[CH3:28])=[CH:23][CH:22]=1.Cl>O1CCCC1>[Br:13][C:9]1[CH:8]=[C:7]([C:27]([C:24]2[CH:25]=[CH:26][C:21]([OH:20])=[CH:22][CH:23]=2)=[CH2:28])[CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of n-butyllithium (1.6 M solution in hexane, 41.6 mL, 1.1 eq) was added dropwise to a solution of 1,3-dibromobenzene (7.6 mL, 1.1 eq) in tetrahydrofuran (30 mL) at −78° C. After stirring 30 min at −78° C. 1-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-ethanone (12.6 g, 57 mmol, 1 eq) in tetrahydrofuran (25 mL) was added dropwise. The mixture was allowed to warm up to room temperature and stirred for 2 h, then treated with 1 N HCl (10 mL), extracted with ethyl acetate, dried (sodium sulfate) and concentrated in vacuo. The crude was dissolved in toluene (40 mL) and p-toluenesulfonic acid (50 mg) was added. The mixture was heated at 150° C. for 3 h. The solvent was removed under reduce pressure and the residue was purified by column chromatography (cyclohexane) to afford the title compound as a colorless oil (1.2 g, 10%);

Workup

temperatureto warm up to room temperature
stirringstirred for 2 h
extractionextracted with ethyl acetate
dry with materialdried (sodium sulfate)
concentrationconcentrated in vacuo
dissolutionThe crude was dissolved in toluene (40 mL)
additionp-toluenesulfonic acid (50 mg) was added
temperatureThe mixture was heated at 150° C. for 3 h
customThe solvent was removed
customthe residue was purified by column chromatography (cyclohexane)

Sources & evidence

ORD record: ord-53c1af652b41470d9e448ad48d44c98c
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989449B2

Reaction notes

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