Water → HCID 68430928, compound

HRID 889255Notes

Reaction equation

HRID 889255 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C>[CH2:18]([O:5][C:4](=[O:6])[C:3]1[C:2]([F:1])=[CH:10][CH:9]=[CH:8][C:7]=1[O:11][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl Bromide2×HCID 11430Potassium CarbonateHCID 5867772-Fluoro-6-hydroxybenzoic acid

Product 1

HCID 68430928HCID 68430928, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2.6 g (16.7 mmol) of 2-fluoro-6-hydroxybenzoic acid and 6.90 g (50 mmol) of potassium carbonate in 15 mL DMF is slowly added 8.5 g (50 mmol) of benzyl bromide. The mixture is stirred at room temperature for 5 h. Another 1 g of benzyl bromide is added and the mixture is stirred at RT for 18 h. The mixture is poured into water and is extracted with ethyl acetate. The organic phase is washed (3×) with water and 1× with saturated NaCl. The solution is dried over sodium sulfate and the solvent removed under vacuum. The residual oil is purified by flash chromatography to give the product. This is used directly in the next step.

Workup

  1. stirringthe mixture is stirred at RT for 18 h
  2. extractionis extracted with ethyl acetate
  3. washThe organic phase is washed (3×) with water and 1× with saturated NaCl
  4. dry with materialThe solution is dried over sodium sulfate
  5. customthe solvent removed under vacuum
  6. customThe residual oil is purified by flash chromatography
  7. customto give the product

Sources & evidence

ORD record
ord-876e7ea10bf444f6b7a525d080b3ffea
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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