Water → N-[2-(3,3-dimethylbut-1-ynyl)phenyl]acetamide

HRID 1359946Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6].[CH3:12][C:13]([CH3:17])([CH3:16])[C:14]#[CH:15].O>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:12][C:13]([CH3:17])([CH3:16])[C:14]#[C:15][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6]

Participants

Conditions

Temperature: 50 °C

Procedure

Under argon, 25.7 g (120 mmol) of ortho-bromoacetanilide, 5.05 g (7.2 mmol) of bis(triphenylphosphine)palladium(II) chloride and 1.37 g (7.2 mmol) of copper(I) iodide were initially charged in 450 ml of triethylamine. At room temperature, 17.8 g (180 mmol) of 3,3-dimethyl-1-butyne were then added dropwise over a period of 10 min, and the mixture is stirred at 50° C. for 5 h. The reaction mixture was poured into 2 l of water and extracted 3 times with in each case 250 ml of diethyl ether, and the extracts were dried over sodium sulphate and concentrated. Column-chromatographic purification on silica gel 60 with methylene chloride gave 25.9 g of N-[2-(3,3-dimethylbut-1-ynyl)-phenyl]acetamide of logP (pH 2.3)=3.03.

Workup

extractionextracted 3 times with in each case 250 ml of diethyl ether
dry with materialthe extracts were dried over sodium sulphate
concentrationconcentrated
customColumn-chromatographic purification on silica gel 60 with methylene chloride

Sources & evidence

ORD record: ord-0061bc25fdb74472bde1c4694bd5b609
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879760B2

Reaction notes

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