Sodium Carbonate → HCID 90418324, compound

HRID 2177358Notes

Reaction equation

HRID 2177358 reaction equation
Br[C:2]1[C:6]([CH:7]=[O:8])=[CH:5][S:4][CH:3]=1.[CH2:9]([C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1)[CH3:10].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.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:16]=[CH:15][C:14]([C:2]2[C:6]([CH:7]=[O:8])=[CH:5][S:4][CH:3]=2)=[CH:13][CH:12]=1)[CH3:10]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734352Boronic acid, (4-ethylphenyl)-HCID 27642074-Bromothiophene-3-carboxaldehyde

Product 1

HCID 90418324HCID 90418324, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
128 °C

Procedure

A mixture of 3-bromo-4-formylthiophene (0.62 g, 3.18 mmol) and 4-ethylphenylboronic acid (0.95 g, 6.36 mmol) in toluene (12 mL), EtOH (12 mL) and aqueous Na2CO3 solution (2 M, 3.18 mL, 6.36 mmol) in a seal tube was deoxygenated under reduced pressure and flushed with argon for 3 times, followed by addition of Pd(PPh3)4 (184 mg, 0.16 mmol) and deoxygenated again. The resulting solution was stirred at 128° C. in an oil bath for 5 hour. The reaction progress was monitored by TLC/LCMS (ethyl acetate/petroleum ether=1:6). The reaction was partitioned between ethyl acetate and water. Collected the organic phases and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10). This resulted in 440 mg (64%) of 4-(4-ethylphenyl)thiophene-3-carbaldehyde as light yellow oil.

Workup

  1. customwas deoxygenated under reduced pressure
  2. customflushed with argon for 3 times
  3. customdeoxygenated again
  4. customThe reaction was partitioned between ethyl acetate and water
  5. customCollected the organic phases
  6. concentrationconcentrated under vacuum
  7. customThis resulted in 440 mg (64%) of 4-(4-ethylphenyl)thiophene-3-carbaldehyde as light yellow oil

Sources & evidence

ORD record
ord-9f962bcf9f424f57b33de79eeba82094
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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