2,6-Dibromophenol → HCID 59382965, compound

HRID 1254401Notes

Reaction equation

HRID 1254401 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[OH:9].[CH3:10][CH:11]([CH3:15])[CH2:12][C:13]#[CH:14]>N1C=CC=CC=1>[Br:8][C:4]1[C:3]2[O:9][C:13]([CH2:12][CH:11]([CH3:15])[CH3:10])=[CH:14][C:2]=2[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 118472,6-DibromophenolHCID 1389484-Methyl-1-pentyne

Product 1

HCID 59382965HCID 59382965, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred mixture of 2,6-dibromophenol (946 mg, 3.76 mmol), Cu2O (322 mg, 2.25 mmol), 4-methylpentyne (0.5 mL, 3.9 mmol) and pyridine (5 mL) was heated at vigorous reflux for 0.5 h. The mixture was concentrated under reduced pressure to remove pyridine, diluted with ether (100 mL), washed with water (50 mL), 5% aq HCl (2×50 mL) and 1M aq NaOH (50 mL) and dried over MgSO4. Removal of the solvent left an oil (650 mg) containing 7-bromo-2-isobutylbenzofuran (˜70% pure).

Workup

  1. temperaturewas heated
  2. temperatureat vigorous reflux for 0.5 h
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customto remove pyridine
  5. additiondiluted with ether (100 mL)
  6. washwashed with water (50 mL), 5% aq HCl (2×50 mL) and 1M aq NaOH (50 mL)
  7. dry with materialdried over MgSO4
  8. customRemoval of the solvent
  9. waitleft an oil (650 mg)
  10. additioncontaining 7-bromo-2-isobutylbenzofuran (˜70% pure)

Sources & evidence

ORD record
ord-cbc607582ce14c20a009664d9736a9a1
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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