1-Ethynyl-4-fluorobenzene → HCID 14716423, compound

HRID 1886302Notes

Reaction equation

HRID 1886302 reaction equation
Cl.O[NH3+].[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[CH:12])=[CH:7][CH:6]=1.[CH2:13]([C:18]1[CH:23]=[CH:22][C:21]([C:24]#[C:25]Br)=[CH:20][CH:19]=1)[CH2:14][CH2:15][CH2:16][CH3:17]>C(N)C.CO.O.Cl[Cu]>[CH2:13]([C:18]1[CH:19]=[CH:20][C:21]([C:24]#[C:25][C:12]#[C:11][C:8]2[CH:9]=[CH:10][C:5]([F:4])=[CH:6][CH:7]=2)=[CH:22][CH:23]=1)[CH2:14][CH2:15][CH2:16][CH3:17]

Participants

8

Reactant 3

HCID 5226271-Ethynyl-4-fluorobenzeneHCID 14716422HCID 14716422, compoundHCID 22029257Hydroxyammonium hydrochloride

Product 1

HCID 14716423HCID 14716423, compound

Reagents, catalysts & solvents 4

HCID 62652Cuprous chlorideCatalystHCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6341EthylamineSolvent

Procedure

A solution of 0.2 g of CuCl and 0.5 g of hydroxylammonium hydrochloride in 16 ml of 50% aqueous ethylamine is added to a solution of 0.1 m of 4-fluorophenylacetylene in 100 ml of methanol. 0.1 m of p-n-pentylphenylbromoethyne dissolved in methanol is added dropwise under a nitrogen atmosphere and with stirring, the mixture is stirred for one hour, diluted with water and extracted with ether, and the extracts are washed until neutral. Customary work-up gives 1-p-n-pentylphenyl-4-p-fluorophenylbutadiyne.

Workup

  1. additionis added dropwise under a nitrogen atmosphere
  2. stirringthe mixture is stirred for one hour
  3. extractionextracted with ether
  4. washthe extracts are washed until neutral

Sources & evidence

ORD record
ord-3ff0a2cf2f1c48fe9a7dc3cde68271ef
Source dataset
uspto-grants-1992_09
Patent number
US05151213

Reaction notes

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