Bromopentafluorobenzene → HCID 54473349, compound
Reaction equation
Br[C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12].[CH2:13]([OH:17])[CH2:14][C:15]#[CH:16].COC(C)(C)C>C(N(CC)CC)C.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:8][C:7]1[C:2]([C:16]#[C:15][CH2:14][CH2:13][OH:17])=[C:3]([F:12])[C:4]([F:11])=[C:5]([F:10])[C:6]=1[F:9]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 1-bromo-2,3,4,5,6-pentafluorobenzene (50 g) in triethylamine (200 mL), 3-butyn-1-ol (15 g), triphenylphosphine (2.7 g), dichlorobistriphenylphosphinepalladium (3.6 g) and copper (I) iodide (1.9 g) were added, followed by stirring at 80° C. for 16 hours. The reaction mixture was cooled to room temperature, and tert-butyl methyl ether (500 mL) was added thereto, followed by stirring at 0° C. for 30 minutes. The reaction mixture was filtered through “Celite” (registered trademark), and the filtrate was concentrated. The resulting residue was purified by flash column chromatography (hexane:ethyl acetate=95:5→65:35) to give the title compound (43 g) having the following physical properties.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- stirringby stirring at 0° C. for 30 minutes
- filtrationThe reaction mixture was filtered through “Celite” (registered trademark)
- concentrationthe filtrate was concentrated
- customThe resulting residue was purified by flash column chromatography (hexane:ethyl acetate=95:5→65:35)
Sources & evidence
- ORD record
- ord-dcebf366dbd94ab49f3bdcfc788b6497
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08115014B2
Reaction notes
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