Hydrochloric Acid → HCID 12990911, compound

HRID 1827972Notes

Reaction equation

HRID 1827972 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([O:12]CC)=[O:11])=[CH:7][C:6]=2[CH:15]=1.[S:16]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17]1.C(=O)([O-])[O-].[Na+].[Na+].Cl>O.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.O1CCOCC1>[S:16]1[CH:20]=[CH:19][C:18]([C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][C:6]=3[CH:15]=2)=[CH:17]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 735184Ethyl (5-bromobenzofuran)-2-carboxylate

Product 1

HCID 12990911HCID 12990911, compoundYield 97.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 5-bromobenzofuran-2-carboxylate 15 (1.0 g, 3.7 mmole), 3-thiopheneboronic acid (0.52 g, 4.1 mmole), tetrakis(triphenylphosphine)palladium (0) (47 mg), sodium carbonate (1.30 g, 12.3 mmole) in water (10 ml), and dioxane (10 ml) was stirred under an atmosphere of argon and heated to 100° C. for 24 hrs. The mixture was cooled, acidified with 1M HCl, extracted with ethyl acetate, washed with water, dried, and evaporated, to give about 0.88 g of 5-thiophen-3-yl-benzofuran-2-carboxylic acid 21, mp. 215–220° C.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-5d1f3ed484d24c7bba64bc1a1803f03a
Source dataset
uspto-grants-2006_06
Patent number
US07056903B2

Reaction notes

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