HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Trimethylsilylacetylene → Methyl 2-chloro-5-((trimethylsilyl)ethynyl)benzoate

HRID 1988369
Notes
Print preview

Reaction equation

HRID 1988369 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](I)[CH:7]=[CH:6][C:5]=1[Cl:11].[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15]>C(N(CC)CC)C.Cl[Pd-2](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)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[CH:7]=[CH:6][C:5]=1[Cl:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 35563912Methyl 2-chloro-5-iodobenzoate

Product 1

HCID 57422929Methyl 2-chloro-5-((trimethylsilyl)ethynyl)benzoateYield 98.1%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 83717Copper iodideCatalyst
HCID 178418903
HCID 178418903, compound
Catalyst
HCID 8471TriethylamineSolvent

Procedure

A mixture of 2-chloro-5-iodo-benzoic acid methyl ester (3.5 g, 12 mmol), dichlorobis(triphenylphosphino)palladium (II) (0.04 g, 0.06 mmol), triphenylphosphine (0.06 g, 0.24 mmol), copper iodide (0.05 g, 0.24 mmol), (trimethylsilyl)acetylene (1.9 g, 19.2 mmol) in triethylamine (40 mL) was heated at reflux for 12 h. The mixture was concentrated in vacuo, diluted with ethyl acetate (150 mL) and washed sequentially with 10% aqueous citric acid, water, and brine. The organic solution was dried, filtered and concentrated in vacuo to afford the title compound (3.14 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 h
  3. concentrationThe mixture was concentrated in vacuo
  4. additiondiluted with ethyl acetate (150 mL)
  5. washwashed sequentially with 10% aqueous citric acid, water, and brine
  6. customThe organic solution was dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-264d5db6b1a74ad7b9bdffb802943d4d
Source dataset
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07553972B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes