4-Fluoroiodobenzene → 4-(4-Fluorophenyl)but-3-yn-1-ol

HRID 1165271Notes

Reaction equation

HRID 1165271 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH2:9]([OH:13])[CH2:10][C:11]#[CH:12]>C(NCC)C.[Cu]I>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]#[C:11][CH2:10][CH2:9][OH:13])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 96054-FluoroiodobenzeneHCID 135663-Butyn-1-OL

Product 1

HCID 124784404-(4-Fluorophenyl)but-3-yn-1-olYield 34.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8021DiethylamineSolvent

Procedure

Copper (I) iodide was added to a stirred solution of 1-fluoro-4-iodobenzene (11.09 g), 3-butyn-1-ol (3.5 g), and BTPC (100 g) in diethylamine (70 ml) and the mixture stirred under nitrogen for 16 h. The mixture was evaporated in vacuo and purified by FCC on eluting with H - EA (2:1) gave the title compound as a yellow solid (2.8 g). T.l.c. (H - EA 2:1) RF 0.20.

Workup

  1. customThe mixture was evaporated in vacuo
  2. custompurified by FCC
  3. washon eluting with H - EA (2:1)

Sources & evidence

ORD record
ord-25934e96c9a34d6b9c41560041e03173
Source dataset
uspto-grants-1990_03
Patent number
US04908386

Reaction notes

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