4-Bromoanisole → 1-Ethynyl-4-methoxybenzene

HRID 428653Notes

Reaction equation

HRID 428653 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C[Si]([C:14]#[CH:15])(C)C.[OH-].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.CN(C=O)C.CCN(CC)CC>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:14]#[CH:15])=[CH:3][CH:4]=1

Participants

8

Reactant 3

HCID 77304-BromoanisoleHCID 14797Potassium HydroxideHCID 66111Trimethylsilylacetylene

Product 1

HCID 2510201-Ethynyl-4-methoxybenzene

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Using Method D above, 4-bromoanisole (Aldrich) was coupled with trimethylsilylacetylene (Aldrich) using (Ph3P)2PdCl2 and CuI as catalyst in DMF and Et3N as solvent and was heated at reflux for 1 day. The resulting trimethylsilyl derivative was hydrolized with aqueous potassium hydroxide to give 4-methoxyphenyl acetylene.

Workup

  1. temperatureat reflux for 1 day

Sources & evidence

ORD record
ord-a517a2329fe34fdead8c15b65bc6b3c3
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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