Sodium Carbonate → HCID 22634660, compound

HRID 1057956Notes

Reaction equation

HRID 1057956 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:6]=1.[C:12]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23])([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[Na+].[Na+]>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.C1(C)C=CC=CC=1>[C:12]([C:16]1[CH:17]=[C:18]([C:2]2[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:6]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 106321513-Tert-butyl-4-methoxyphenylboronic acidHCID 15293216Ethyl 5-bromothiophene-3-carboxylate

Product 1

HCID 22634660HCID 22634660, compoundYield 101.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

260 mg (0.5 mmol) of tetrakis(triphenylphosphine)palladium(0), 50 ml of toluene and 2.59 g (10.9 mmol) of ethyl 2-bromo-4-thiophenecarboxylate are introduced into a three-necked flask under a stream of nitrogen and the mixture is stirred at room temperature for 20 minutes. 3.7 g (16.5 mmol) of 3-tert-butyl-4-methoxyphenylboronic acid and 11 ml of aqueous sodium carbonate solution (2 N) are then added and the mixture is refluxed for 8 hours. The reaction medium is evaporated to dryness, the residue is taken up in water and ethyl ether and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue is purified by chromatography on a column of silica eluted with a mixture of ethyl acetate and heptane (10/90% by volume). 3.53 g (69%) of ethyl 2-(3-tert-butyl-4-methoxyphenyl)-4-thiophenecarboxylate are obtained.

Workup

  1. temperaturethe mixture is refluxed for 8 hours
  2. customThe reaction medium is evaporated to dryness
  3. customethyl ether and the organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue is purified by chromatography on a column of silica
  7. washeluted with a mixture of ethyl acetate and heptane (10/90% by volume)

Sources & evidence

ORD record
ord-ffc3ff25127349f3a6e248030877d86f
Source dataset
uspto-grants-2003_02
Patent number
US06515021B1

Reaction notes

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