Ethanol → HCID 10402349, compound

HRID 1408305Notes

Reaction equation

HRID 1408305 reaction equation
[Br:1][C:2]1[S:3][C:4](Br)=[CH:5][CH:6]=1.[CH3:8][C:9]1[CH:14]=[CH:13][C:12](B(O)OC(O)=O)=[CH:11][CH:10]=1.[C:21]([O-])([O-])=[O:22].[K+].[K+].CC[OH:29]>C1(C)C=CC=CC=1.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>[CH3:21][O:22][C:8](=[O:29])[C:9]1[CH:10]=[CH:11][C:12]([C:4]2[S:3][C:2]([Br:1])=[CH:6][CH:5]=2)=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 184532,5-DibromothiopheneHCID 67375032HCID 67375032, compound

Product 1

HCID 10402349HCID 10402349, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 2,5-dibromothiophene (1.0 g, 4.1 mmol), 4-methylcarboxyphenylboronic acid (370 mg, 2.05 mmol), Pd(PPh3)4 (30 mg) and K2CO3 (1.13 g, 8.2 mmol) in toluene (20 mL) containing 5 mL EtOH and 1 mL water were refluxed overnight under argon. After cooling to room temperature, the solvent was evaporated and residue partitioned between EtOAc and water. Organic layer was separated, dried, evaporated and residue purified by combiflash to afford 4-(5-Bromo-thiophen-2-yl)-benzoic acid methyl ester (200 mg) which was redissolved in toluene (10 mL), containing 4-hexyloxyphenylboronic acid (222 mg, 0.1 mmol), Pd(PPh3)4 (30 mg) and K2CO3 (189 mg, 0.13 mmol) containing 3 mL EtOH and 0.5 mL water and refluxed overnight. The resulting solution was cooled and the solid formed filtered, washed with water and methanol and dried (130 mg). It was subjected to hydrolysis using dioxane-water/NaOH overnight to afford 4-[5-(4-Hexyloxy-phenyl)-thiophen-2-yl]-benzoic acid

Workup

  1. temperaturewere refluxed overnight under argon
  2. customthe solvent was evaporated
  3. customresidue partitioned between EtOAc and water
  4. customOrganic layer was separated
  5. customdried
  6. customevaporated
  7. customresidue purified by combiflash

Sources & evidence

ORD record
ord-1f66c84a5678467fa84509b8a5affa46
Source dataset
uspto-grants-2014_12
Patent number
US08921309B2

Reaction notes

Loading…