Triethylamine → HCID 59536255, compound

HRID 1181400Notes

Reaction equation

HRID 1181400 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=[O:5].[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].C(N(CC)CC)C>CN(C)C=O.[Cu]I.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>[F:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([C:16]#[C:15][Si:12]([CH3:14])([CH3:13])[CH3:11])[C:3]=1[CH:4]=[O:5]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 224739772-Bromo-6-fluorobenzaldehyde

Product 1

HCID 59536255HCID 59536255, compoundYield 95.6%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 2-bromo-6-fluorobenzaldehyde (Description 39; 10.0 g, 49.3 mmol) and (trimethylsilyl) acetylene (13.94 ml, 98.6 mmol) in anhydrous N,N-dimethylformamide (250 ml) under an atmosphere of nitrogen was added triethylamine (10.25 ml, 73.95 mmol), copper (I) iodide (0.94 g, 4.93 mmol) and Pd(PPh3)2Cl2 (1.73 g, 2.47 mmol). The mixture was degassed and stirred at room temperature overnight. The mixture was poured into water (600 ml) and extracted with ethyl acetate (3×200 ml). The combined organic layers were washed with water (3×300 ml), brine (200 ml) then dried over Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel eluting with 5% Et2O in iso-hexanes to give the title compound (10.38 g, 95%).

Workup

  1. customThe mixture was degassed
  2. additionThe mixture was poured into water (600 ml)
  3. extractionextracted with ethyl acetate (3×200 ml)
  4. washThe combined organic layers were washed with water (3×300 ml), brine (200 ml)
  5. dry with materialthen dried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel eluting with 5% Et2O in iso-hexanes

Sources & evidence

ORD record
ord-619532a3b5ac4f41ac87106e9e6fb40a
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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