1-Iodo-4-(trifluoromethoxy)benzene → 2,2-Dimethyl-5-(4-trifluoromethoxy-phenyl)-pent-4-yn-1-ol

HRID 852390Notes

Reaction equation

HRID 852390 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[CH3:13][C:14]([CH3:20])([CH2:17][C:18]#[CH:19])[CH2:15][OH:16]>N1CCCCC1.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.[Cu]I>[CH3:13][C:14]([CH3:20])([CH2:17][C:18]#[C:19][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1)[CH2:15][OH:16]

Participants

6

Reactant 2

HCID 27772941-Iodo-4-(trifluoromethoxy)benzeneHCID 112979482,2-Dimethylpent-4-yn-1-ol

Product 1

HCID 688212542,2-Dimethyl-5-(4-trifluoromethoxy-phenyl)-pent-4-yn-1-ol

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8082PiperidineSolvent2×

Conditions

Temperature
50 °C

Procedure

To a degassed (argon) solution of 3.56 g (12.00 mmol) 1-iodo-4-trifluoromethoxy-benzene in 40 ml piperidine was added 0.58 g (0.50 mmol) Pd(PPh3)4 and 0.095 g. (0.50 mmol) CuI. The reaction mixture was stirred at 50° C. for 10 min, then 1.25 g (10.00 mmol) of above synthesized 2,2-dimethyl-pent-4-yn-1-ol in 20 ml of piperidine was added dropwise within 1 h. During the addition the oil bath was slowly heated to 80° C. starting after 30 min. The reaction mixture was stirred at this temperature for 2 h and then extracted with chilled aqueous 10% KHSO4/ether (three times). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated. Purification by flash-chromatography on silica gel (n-heptane/EtOAc 2:1 to 1:1) yielded 1.91 g of the title compound as a yellow oil.

Workup

  1. additionwas added dropwise within 1 h
  2. additionDuring the addition the oil bath
  3. temperaturewas slowly heated to 80° C.
  4. waitstarting after 30 min
  5. stirringThe reaction mixture was stirred at this temperature for 2 h
  6. extractionextracted with chilled aqueous 10% KHSO4/ether (three times)
  7. washThe organic phases were washed with aqueous 10% NaCl
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customPurification by flash-chromatography on silica gel (n-heptane/EtOAc 2:1 to 1:1)

Sources & evidence

ORD record
ord-57ca3b70da104aa989ddd73b95e6849a
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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