5'-Bromo-2'-hydroxyacetophenone → HCID 58423820, compound

HRID 1408826Notes

Reaction equation

HRID 1408826 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[OH:11])(=[O:3])[CH3:2].[O:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[CH2:17][CH:18]=O>CO>[Br:10][C:8]1[CH:9]=[C:4]2[C:5](=[CH:6][CH:7]=1)[O:11][CH:18]([CH2:17][CH:13]1[CH2:14][CH2:15][CH2:16][O:12]1)[CH2:2][C:1]2=[O:3]

Participants

4

Reactant 2

HCID 959915'-Bromo-2'-hydroxyacetophenoneHCID 123850682-(Oxolan-2-yl)acetaldehyde

Product 1

HCID 58423820HCID 58423820, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of 2-Acetyl-4-bromophenol (1.754 g, 8.16 mmol), 2-(tetrahydrofuran-2-yl)acetaldehyde (2.1 g) and purrolidine (0.4 mL) in MeOH was heated to reflux for 2 h. The reaction mixture was cool down to room temperature and evaporated. The residue was dissolved in EA, washed with 1 M HCl, 1 M NaOH (2×50 mL), brine (100 mL) successively, then, dried over anhydrous Na2SO4, and filtered, and concentrated. The residue was purified by flash chromatography on silica gel eluting with EA in hexane (0-20%) to give 6-bromo-2-((tetrahydrofuran-2-yl)methyl)chroman-4-one (464 mg); MS ESI+ve m/z 311 (M+H)+.

Workup

  1. temperatureto reflux for 2 h
  2. customevaporated
  3. dissolutionThe residue was dissolved in EA
  4. washwashed with 1 M HCl, 1 M NaOH (2×50 mL), brine (100 mL) successively
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel eluting with EA in hexane (0-20%)

Sources & evidence

ORD record
ord-9caeb94c788f4678b4a018927be93816
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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