1-Butyne → 1-But-1-ynyl-4-fluoro-2-methoxymethoxy-benzene

HRID 423179

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH2:10][O:11][CH3:12].[CH:13]#[C:14][CH2:15][CH3:16]>C(NCC)C.CCOCC.[Cu]I.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>[C:13]([C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH2:10][O:11][CH3:12])#[C:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: 70 °C

Procedure

1-Bromo-4-fluoro-2-methoxymethoxy-benzene (7.6 g, 32 mmol) is placed in a pressure flask, dissolved in diethylamine (65 mL) and degassed with nitrogen for 15 min. An excess of butyne is bubbled through the solution, CuI (1.9 g, 10 mmol) and PdCl2(PPh3)2 (2.3 g, 3.3 mmol) are added, and the flask is heated to 70° C. for 44 h. The mixture is diluted with ether, then washed with saturated aqueous NH4Cl and brine. The organic portion is dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (Biotage® Si65M, 3% THF/hexane) to provide 6.12 g (91%) of the title compound as an orange solid. GCMS m/e 208 [M]+.

Workup

customdegassed with nitrogen for 15 min
additionare added
washwashed with saturated aqueous NH4Cl and brine
dry with materialThe organic portion is dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting residue is purified by flash chromatography (Biotage® Si65M, 3% THF/hexane)

Sources & evidence

ORD record: ord-bc3a652c23944c49801cf9ef32298cc6
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101761B2

Linked notes

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