Potassium Carbonate → 6-Bromo-4-(4-hydroxy-benzyl)-7-methoxy-3-(4-trifluoromethyl-phenyl)-chromen-2-one

HRID 1296696Notes

Reaction equation

HRID 1296696 reaction equation
[Br:1][C:2]1[C:3]([O:19][CH3:20])=[CH:4][C:5]([OH:18])=[C:6]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:7]=1.[F:21][C:22]([F:34])([F:33])[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](O)=[O:31])=[CH:25][CH:24]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:19][CH3:20])[O:18][C:30](=[O:31])[C:29]([C:26]1[CH:25]=[CH:24][C:23]([C:22]([F:21])([F:33])[F:34])=[CH:28][CH:27]=1)=[C:8]2[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 589131241-(5-Bromo-2-hydroxy-4-methoxy-phenyl)-2-(4-hydroxy-phenyl)-ethanone

Product 1

HCID 589131126-Bromo-4-(4-hydroxy-benzyl)-7-methoxy-3-(4-trifluoromethyl-phenyl)-chromen-2-oneYield 85.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(5-bromo-2-hydroxy-4-methoxy-phenyl)-2-(4-hydroxy-phenyl)-ethanone (0.64 g, 1.9 mmol), 4-trifluoromethylphenylacetic acid (0.78 g, 3.8 mmol), carbonyl diimidazole (0.62 g, 3.8 mmol), N,N-dimethylaminopyridine (0.12 g, 1.0 mmol), and potassium carbonate (0.52 g, 3.8 mmol) in DMF (15 mL) was heated within an 80° C. oil bath overnight. The cooled reaction mixture was poured into water and extracted with EtOAc. Organic extracts were combined and washed with water and saturated sodium chloride in succession, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting material purified using silica gel flash column chromatography (1:2 EtOAc:hexanes) to provide the title compound (0.82 g, 85%). MS (ESI) m/z 505.0 (M+1)+, 507.0 (M+1+2)+.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with EtOAc
  3. washwashed with water and saturated sodium chloride in succession
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting material purified

Sources & evidence

ORD record
ord-f74eb17b4620424ab11034f3612f1096
Source dataset
uspto-grants-2007_07
Patent number
US07247646B2

Reaction notes

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