Bromine → 1-(5-Bromo-2-hydroxy-4-methoxy-phenyl)-2-(4-hydroxy-phenyl)-ethanone

HRID 1296695Notes

Reaction equation

HRID 1296695 reaction equation
[Br:1]Br.[OH:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[C:12](=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:1][C:7]1[C:8]([O:10][CH3:11])=[CH:9][C:4]([OH:3])=[C:5]([C:12](=[O:21])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 149200561-(2-Hydroxy-4-methoxyphenyl)-2-(4-hydroxyphenyl)ethanone

Product 1

HCID 589131241-(5-Bromo-2-hydroxy-4-methoxy-phenyl)-2-(4-hydroxy-phenyl)-ethanoneYield 18.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (3.6 mL, 75.6 mmol) in acetic acid (50 mL) was added dropwise to a stirring solution of 1-(2-hydroxy-4-methoxy-phenyl)-2-(4-hydroxy-phenyl)-ethanone (20 g, 77.4 mmol) in acetic acid (500 mL), and the reaction mixture was allowed to stir for 8 h. The acetic acid was then removed under reduced pressure, and the resulting solid was recrystallized from methanol/water to provide 8.9 g of crude product. Further purification using reverse-phase preparatory HPLC (30–100% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 18 min, then at 100% acetonitrile for 15 min) provided fractions that were subsequently neutralized with sodium bicarbonate and extracted using ethyl acetate. The organic fractions were combined, dried over magnesium sulfate and filtered, and the solvent was removed under reduced pressure to afford the title compound (4.8 g, 18%). MS (ESI) m/z 337.3 (M+1)+, 339.3 (M+1+2)+.

Workup

  1. customThe acetic acid was then removed under reduced pressure
  2. customthe resulting solid was recrystallized from methanol/water
  3. customto provide 8.9 g of crude product
  4. customFurther purification
  5. waitover 18 min
  6. customat 100% acetonitrile for 15 min) provided fractions that
  7. extractionextracted
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9809de0807a9481c934b9603b80d6f7c
Source dataset
uspto-grants-2007_07
Patent number
US07247646B2

Reaction notes

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