Trimethylsilylacetylene → tert-Butyl 4-((trimethylsilyl)ethynyl)benzoate

HRID 974207Notes

Reaction equation

HRID 974207 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1Br)([CH3:4])([CH3:3])[CH3:2].[CH3:15][Si:16]([C:19]#[CH:20])([CH3:18])[CH3:17].C(Cl)Cl.O>C(#N)C.C(N(CC)CC)C.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>[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([C:20]#[C:19][Si:16]([CH3:18])([CH3:17])[CH3:15])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 3804415tert-Butyl 2-bromobenzoateHCID 21908982Water methylene chloride

Product 1

HCID 13965007tert-Butyl 4-((trimethylsilyl)ethynyl)benzoateYield 74%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

51.4 g of Bromobenzoic acid tert.-butyl ester, 21.6 g of trimethylsilylacetylene, 1.4 g of (Ph3P)2PdCl2 in 400 ml of absolute acetonitrile and 100 ml of triethylamine are stirred under reflux for 8 hours in an atmosphere of nitrogen. After the reaction product has been worked up with CH2Cl2 /H2O and distilled, 40.6 g of 4-(trimethylsilylethinyl)-benzoic acid tert.-butyl ester are obtained.

Workup

  1. temperatureunder reflux for 8 hours in an atmosphere of nitrogen
  2. distillationdistilled

Sources & evidence

ORD record
ord-eee2de486c8f4e54bde9c82d3a19703a
Source dataset
uspto-grants-1991_11
Patent number
US05068300

Reaction notes

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