Phenylboronic Acid → HCID 21220939, compound

HRID 1584790Notes

Reaction equation

HRID 1584790 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:11]=[O:12])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(COC)OC.C(=O)(O)[O-].[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>[C:13]1([C:2]2[CH:3]=[C:4]([CH:11]=[O:12])[C:5]3[O:9][CH:8]=[CH:7][C:6]=3[CH:10]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 66827Phenylboronic AcidHCID 212208405-Bromo-1-benzofuran-7-carbaldehyde

Product 1

HCID 21220939HCID 21220939, compoundYield 36.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 5-bromo-benzofuran-7-carbaldehyde (600 mg), phenylboronic acid (326 mg) and tetrakis(triphenylphosphine)palladium (O) (176 mg) in dimethoxyethane (20 ml) and 8% sodium bicarbonate (10 ml) was heated at reflux for 16 h. Solvent was removed in vacuo, the residue was partitioned between chloroform (40 ml) and water (40 ml). The organic phase was washed with brine (50 ml), dried, filtered and the filtrate evaporated in vacuo to give a yellow oil. Purification by FCC eluted with hexane:ethyl acetate (1:0→10:1) gave the title compound as a pale yellow solid (214 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. customSolvent was removed in vacuo
  4. customthe residue was partitioned between chloroform (40 ml) and water (40 ml)
  5. washThe organic phase was washed with brine (50 ml)
  6. customdried
  7. filtrationfiltered
  8. customthe filtrate evaporated in vacuo
  9. customto give a yellow oil
  10. customPurification by FCC
  11. washeluted with hexane:ethyl acetate (1:0→10:1)

Sources & evidence

ORD record
ord-24609744fb44491bbad8523c464606b6
Source dataset
uspto-grants-1999_08
Patent number
US05935972

Reaction notes

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