Hydrochloric Acid → 5-Phenyl-2-benzofurancarboxylic acid

HRID 2120580Notes

Reaction equation

HRID 2120580 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 15 (2.5 g, 9.3 mmole), benzeneboronic acid (1.25 g, 10.2 mmole), tetrakis(triphenylphosphine)palladium (0) (118 mg), sodium carbonate (3.25 g, 30.6 mmole) in water (25 ml), and dioxane (25 ml) was stirred under an argon atmosphere and heated to 100° C. for 16 hrs. The white heterogeneous mass was acidified with 1M HCl, extracted, washed, dried, and evaporated, to give about 2.2 g of 5-phenyl-benzofuran-2-carboxylic acid 16, mp. 218-220° C.

Workup

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

Sources & evidence

ORD record
ord-c449ce2634624ae389d6099c42b4f538
Source dataset
uspto-grants-2004_02
Patent number
US06693098B2

Reaction notes

Loading…