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

HRID 2096635Notes

Reaction equation

HRID 2096635 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-5f5a667c7e594080b3965a10b4273e8b
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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