4-Bromothiophene-3-carboxaldehyde → HCID 22503031, compound

HRID 1006936Notes

Reaction equation

HRID 1006936 reaction equation
[CH:1]([C:3]1[C:7](Br)=[CH:6][S:5][CH:4]=1)=[O:2].[CH3:9][O:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]#[CH:20])=[CH:15][CH:14]=1>CN(C=O)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(N(CC)CC)C>[CH3:9][O:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:7]2[C:3]([CH:1]=[O:2])=[CH:4][S:5][CH:6]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 27642074-Bromothiophene-3-carboxaldehydeHCID 225029951-Ethynyl-4-(methoxymethoxy)benzene

Product 1

HCID 22503031HCID 22503031, compoundYield 66.9%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

3-Formyl-4-bromothiophene (14.7 g) was dissolved in DMF (100 ml), followed by the addition of triethylamine (100 ml) CuI (0.25 g), Pd(PPh3)2Cl2(0.5 g) and 4-methoxymethoxy-1-ethynylbenzene (11.4 g), and the mixture was reacted at 70° C. overnight. The reaction solution was filtered through Celite, poured into 1N hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with an aqueous solution of saturated sodium bicarbonate and brine, dried and evaporated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system), to give 3-{[4-(methoxymethoxy)phenyl]ethynyl}-4-formylthiophene as a colorless oil (12.8 g, yield; 47%).

Workup

  1. customthe mixture was reacted at 70° C. overnight
  2. filtrationThe reaction solution was filtered through Celite
  3. additionpoured into 1N hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous solution of saturated sodium bicarbonate and brine
  6. customdried
  7. customevaporated
  8. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-ad069d7b217e4c94a3e6947ba873653d
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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