2,6-Dibromophenol → HCID 59598461, compound

HRID 2266233Notes

Reaction equation

HRID 2266233 reaction equation
[CH3:1][C:2]([CH3:6])([CH3:5])[C:3]#[CH:4].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10](Br)[C:9]=1[OH:15]>N1C=CC=CC=1.CCOC(C)=O>[Br:7][C:8]1[C:9]2[O:15][C:3]([C:2]([CH3:6])([CH3:5])[CH3:1])=[CH:4][C:10]=2[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 118472,6-DibromophenolHCID 135123,3-Dimethyl-1-butyne

Product 1

HCID 59598461HCID 59598461, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

3,3-Dimethylbut-1-yne (1.6 g, 20 mmol) was added to a solution of 2,6-dibromophenol (5.0 g, 20 mmol) and Cu2O (1.7 g, 12 mmol) in dry pyridine (50 mL) under N2, then the mixture was heated to about 55° C. and stirred overnight. The mixture was filtered and the filtrate was concentrated to give a residue, which was dissolved in EtOAc. This solution was washed with brine and dried over Na2SO4. The solvent was removed and the residue was purified by column chromatography to afford 7-bromo-2-tert-butyl-benzofuran (1.3 g, 26%). 1H NMR (CDCl3): 1.40 (S, 9H), 6.41 (s, 1H), 7.04 (t, 1H), 7.38 (d, 1H), 7.42 (d, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give a residue, which
  4. washThis solution was washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2a0d80164c34479a93bd4f4d95d0da70
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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