Water → HCID 86646594, compound

HRID 445248Notes

Reaction equation

HRID 445248 reaction equation
[Br:1][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.O>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>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=[O:5].[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

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 224739772-Bromo-6-fluorobenzaldehyde

Product 1

HCID 86646594HCID 86646594, compound

Reagents, catalysts & solvents 3

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

Procedure

A solution of 2-bromo-6-fluorobenzaldehyde (3.3 g, 16 mmol) and (trimethylsilyl)acetylene (4.5 mL, 32 mmol) in anhydrous N,N-dimethylformamide (60 mL) was treated with triethylamine (3.5 mL, 25 mmol), copper(I) iodide (0.3 g, 1.6 mmol), and Pd(PPh3)2Cl2 (0.6 g, 0.80 mmol) under argon atmosphere. The mixture was stirred at RT for 2.5 h. The mixture was poured into water (150 mL) and extracted with ethyl acetate (2×150 mL). The combined organic layers were washed with water (2×75 mL), brine (100 mL) then dried over anhydrous sodium sulfate and evaporated to yield the crude product which was purified by silica gel chromatography (20-30% EtOAc in hexanes) to give 2-fluoro-6-(2-(trimethylsilyl)ethynyl)benzaldehyde 2-bromo-6-fluorobenzaldehyde as a brown oil. MS (ESI, pos. ion) m/z: 221 (M+1).

Workup

  1. extractionextracted with ethyl acetate (2×150 mL)
  2. washThe combined organic layers were washed with water (2×75 mL), brine (100 mL)
  3. dry with materialthen dried over anhydrous sodium sulfate
  4. customevaporated
  5. customto yield the crude product which
  6. customwas purified by silica gel chromatography (20-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-60c93ade35874dccbc7ea329d33bf7f1
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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