Sodium hydride → HCID 86652179, compound

HRID 1944377Notes

Reaction equation

HRID 1944377 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.Br[C:12]1[CH:16]=[CH:15][S:14][C:13]=1[CH:17]=[O:18]>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.C(O)CCC>[F:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:12]2[CH:16]=[CH:15][S:14][C:13]=2[CH:17]=[O:18])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 677894-FluorothiophenolHCID 27970793-Bromothiophene-2-carboxaldehyde

Product 1

HCID 86652179HCID 86652179, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 2631-ButanolSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of sodium hydride (0.20 g) and n-butanol (10 mL) was treated with 4-fluorothiophenol (0.64 g), and the resulting mixture was added to a mixture of 3-bromothiophene-2-carbaldehyde (0.96 g), tetrakis(triphenylphosphine)palladium (0) (0.12 g) and n-butanol (5.0 mL). The resulting mixture was stirred at 100° C. for 2 hours and then at 120° C. for 4 hours. The mixture was cooled to room temperature, concentrated under reduced pressure and the residue partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the combined organic solution was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of cyclohexane and dichloromethane (2:1 to 0:1 by volume) to afford the title compound as a yellow solid (0.78 g).

Workup

  1. waitat 120° C. for 4 hours
  2. temperatureThe mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customthe residue partitioned between water and ethyl acetate
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. dry with materialthe combined organic solution was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel
  9. washeluting with a mixture of cyclohexane and dichloromethane (2:1 to 0:1 by volume)

Sources & evidence

ORD record
ord-5800546df66847cc87fb4d16b9c4bb5b
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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