Tetrahydrofuran → 5-(4'-Ethyl-3-fluorobiphenyl-4-yl)thiophene-2-carbaldehyde

HRID 1943515Notes

Reaction equation

HRID 1943515 reaction equation
Br[C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[CH2:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20](B(O)O)=[C:19]([F:26])[CH:18]=2)=[CH:13][CH:12]=1)[CH3:10].C(=O)([O-])[O-].[Na+].[Na+].C1COCC1>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:9]([C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:2]3[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=3)=[C:19]([F:26])[CH:18]=2)=[CH:15][CH:16]=1)[CH3:10]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 784285-Bromothiophene-2-carbaldehydeHCID 534025754'-Ethyl-3-fluorobiphenyl-4-boronic acid

Product 1

HCID 581606825-(4'-Ethyl-3-fluorobiphenyl-4-yl)thiophene-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 58.5 g (0.31 mol) of 5-bromothiophene-2-carbaldehyde, 75.5 g (0.31 mol) of 4′-ethyl-3-fluoro-4-biphenylboronic acid, 17.0 g (14.7 mmol) of tetrakis(triphenylphosphine)palladium(0) and 375 ml of 2 N sodium carbonate solution in 935 ml of toluene/ethanol (1:1.5) is heated at 80° C. for 1 h. After cooling, the precipitated product is firstly dissolved by addition of THF. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with sat. sodium chloride solution, and the solution is dried using sodium sulfate. The residue remaining after removal of the solvents is digested in toluene, and the product is filtered off, giving 5-(4′-ethyl-3-fluorobiphenyl-4-yl)thiophene-2-carbaldehyde as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. customThe organic phase is separated off
  3. extractionthe aqueous phase is extracted with MTBE
  4. washThe combined organic phases are washed with sat. sodium chloride solution
  5. customthe solution is dried
  6. customafter removal of the solvents
  7. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-f49fa3f2b40e494593479e1b16ae875b
Source dataset
uspto-grants-2013_03
Patent number
US08394293B2

Reaction notes

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