Hydrochloric Acid → 5-Phenyl-2-benzofurancarboxylic acid

HRID 1070384Notes

Reaction equation

HRID 1070384 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.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][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>[C:16]1([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:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 735184Ethyl (5-bromobenzofuran)-2-carboxylate

Product 1

HCID 129909085-Phenyl-2-benzofurancarboxylic acidYield 99.3%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 5-bromo-benzofuran-2-carboxylate (2.5 g, 9.3 mmol), benzeneboronic acid (1.25 g, 10.2 mmol), tetrakis(triphenylphosphine)palladium (0) (118 mg), sodium carbonate (3.25 g, 30.6 mmol) in water (25 mL), and dioxane (25 mL) was stirred under an argon atmosphere and heated to 100° C. for 16 h. The white heterogeneous mass was acidified with 1M HCl, extracted, washed, dried, and evaporated, to give 2.2 g of 5-phenyl-benzofuran-2-carboxylic acid, mp. 218-220° C.

Workup

  1. extractionextracted
  2. washwashed
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-8c23a9ce9ac04db99d69c84f45233f7f
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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