Ethyl Acetate → HCID 10822693, compound

HRID 1006345Notes

Reaction equation

HRID 1006345 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[S:12]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13]1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(COC)OC.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.O>[CH3:11][O:10][C:5]1[CH:4]=[CH:3][C:2]([C:14]2[CH:15]=[CH:16][S:12][CH:13]=2)=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 906845-Bromo-2-methoxybenzaldehydeHCID 581760Thiophene-3-boronic acid

Product 1

HCID 10822693HCID 10822693, compoundYield 81.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Under nitrogen atmosphere, to a solution of 5-bromo-2-methoxybenzaldehyde (350 mg) in dimethoxyethane (3.5 ml) were added 3-thiopheneboronic acid (417 mg), tetrakis(triphenylphosphine)palladium (0) (282 mg), and 2M sodium carbonate (4.9 ml) at room temperature. After being heated at 80° C. with stirring for 5 hours, the reaction mixture was poured into mixed solvents of ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (6 g) using a mixed solvent of hexane and ethyl acetate (10:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give 2-methoxy-5-(3-thienyl)benzaldehyde (290 mg) as yellowish oil.

Workup

  1. additionthe reaction mixture was poured
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by column chromatography on silica gel (6 g)
  7. additionThe fractions containing the objective compound
  8. customwere collected
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6b0b8d47739d4c7aa85927af5c92dcd8
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

Loading…