4-Bromobenzophenone → HCID 66784736, compound

HRID 1095231Notes

Reaction equation

BrC1C=CC([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=CC=1.N1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C[C:23]([OH:27])([C:25]#[CH:26])C.[Cl-].[NH4+].[CH3:30][CH2:31][CH2:32]CCC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:17][C:18]1[C:31]([CH3:32])=[C:30]([C:26]#[C:25][CH2:23][OH:27])[CH:21]=[CH:20][C:19]=1[C:6](=[O:7])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A 30 mL Schlenk tube was replaced with Ar, 3.9 g (15 mmol) of 4-bromobenzophenone, 173 mg (0.15 mmol) of tetrakis(triphenylphosphine)palladium, 15 mL of piperidine and 1.6 mL (16.5 mmol) of 2-methyl-3-butyn-2-ol were added and the mixture was stirred at 100° C. for 1 hour. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and then the mixture was extracted with diethyl ether. The extract was dried over magnesium sulfate, followed by distilling off of the solvent under reduced pressure by an evaporator. The resulting crude reaction product was dissolved in 300 ml of hexane at 70° C., the insolubles were filtered off, and then the filtrate was cooled to give dimethylhydroxymethyl-4-benzoylphenylacetylene, i.e., the desired compound as a yellow crystal. Yield: 3.47 g (yield: 88%).

Workup

additionwere added
extractionthe mixture was extracted with diethyl ether
dry with materialThe extract was dried over magnesium sulfate
distillationby distilling off of the solvent under reduced pressure by an evaporator
customThe resulting crude reaction product
filtrationthe insolubles were filtered off
temperaturethe filtrate was cooled

Sources & evidence

ORD record: ord-1dd95b4a130c440eb6f7dcecd59656c3
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08137821B2

Reaction notes

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