Bromopentafluorobenzene → HCID 54473349, compound

HRID 1908707Notes

Reaction equation

HRID 1908707 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

HCID 9578BromopentafluorobenzeneHCID 135663-Butyn-1-OLHCID 15413tert-Butyl methyl ether

Product 1

HCID 54473349HCID 54473349, compoundYield 89.9%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

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®, 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

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringby stirring at 0° C. for 30 minutes
  3. filtrationThe reaction mixture was filtered through Celite®
  4. concentrationthe filtrate was concentrated
  5. customThe resulting residue was purified by flash column chromatography (hexane:ethyl acetate=95:5→65:35)

Sources & evidence

ORD record
ord-45beca32ee434021b7f5c9e3c577cced
Source dataset
uspto-grants-2013_12
Patent number
US08598223B2

Reaction notes

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