Water → HCID 18471199, compound

HRID 2228647Notes

Reaction equation

HRID 2228647 reaction equation
[S:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.Br[C:10]1[CH:11]=[C:12]([C:15]([F:18])=[CH:16][CH:17]=1)[CH:13]=[O:14].C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.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>[F:18][C:15]1[CH:16]=[CH:17][C:10]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)=[CH:11][C:12]=1[CH:13]=[O:14]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 18471199HCID 18471199, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

1.89 g of 3-thiopheneboronic acid (0.015 mol) are added to a solution of 3-bromo-6-fluorobenzaldehyde (2 g, 0.016 mol) in 35 ml of 1,2-dimethoxyethane, followed by addition of aqueous 2N sodium carbonate solution (3.13 g, 0.030 mol) and a catalytic amount of tetrakis(triphenylphosphine)palladium (0.34 g, 2.96 10−4 mol). The reaction mixture is heated at 80° C. for 20 hours and is then cooled to room temperature and poured into water. The resulting mixture is extracted with ethyl acetate and the organic phase is washed with saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulfate and filtered, and the solvent is evaporated off under reduced pressure. The title product is isolated from the black oil obtained by bulb-to-bulb distillation at 150° C. under reduced pressure (4 10−2 mmbar). 1.36 g of a pale yellow oil which solidifies are isolated.

Workup

  1. temperatureis then cooled to room temperature
  2. extractionThe resulting mixture is extracted with ethyl acetate
  3. washthe organic phase is washed with saturated aqueous sodium chloride solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent is evaporated off under reduced pressure

Sources & evidence

ORD record
ord-27aa0e83d12e423da0ffd9b6acc4ee2f
Source dataset
uspto-grants-2002_07
Patent number
US06417222B1

Reaction notes

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