Diethyl Ether → 3-Fluoro-4-trimethylsilylethynylbenzaldehyde

HRID 346264Notes

Reaction equation

HRID 346264 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[F:10].[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].C(OCC)C>C(N(CC)CC)C>[F:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[C:16]#[C:15][Si:12]([CH3:14])([CH3:13])[CH3:11])[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 66111TrimethylsilylacetyleneHCID 27834114-Bromo-3-fluorobenzaldehyde

Product 1

HCID 199906293-Fluoro-4-trimethylsilylethynylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 4-bromo-3-fluorobenzaldehyde (6 g) in triethylamine (60 ml) was added trimethylsilylacetylene (4.6 ml), bis-triphenylphosphinepalladium dichloride (331 mg) and cuprous iodide (130 mg). The resulting mixture was allowed to stir overnight at room temperature under a nitrogen atmosphere. After this time, diethyl ether was added and the mixture was filtered. The filtrate was washed with water and brine before drying over anhydrous magnesium sulphate and evaporation in vacuo. The resulting oil was crystallised from cold hexane to give 3-fluoro-4-trimethylsilylethynylbenzaldehyde as a light brown solid (4 g).

Workup

  1. filtrationthe mixture was filtered
  2. washThe filtrate was washed with water and brine
  3. dry with materialbefore drying over anhydrous magnesium sulphate and evaporation in vacuo
  4. customThe resulting oil was crystallised from cold hexane

Sources & evidence

ORD record
ord-c5c33a142b1a4df7a961427205d29c26
Source dataset
uspto-grants-1991_10
Patent number
US05061726

Reaction notes

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