Dichloromethane → 4-fluoro-3-phenoxybenzyl (RS)-2-(2-methylpyrimidin-5-yl)-3,3-dimethylbutanoate

HRID 1088312Notes

Reaction equation

HRID 1088312 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Br)=[CH:10][C:9]=1[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:23][C:24]1[N:29]=[CH:28][C:27]([CH:30]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:31]([OH:33])=[O:32])=[CH:26][N:25]=1.ClCCl>CC(C)=O.C(OCC)(=O)C>[CH3:23][C:24]1[N:29]=[CH:28][C:27]([CH:30]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:31]([O:33][CH2:12][C:11]2[CH:14]=[CH:15][C:8]([F:7])=[C:9]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:10]=2)=[O:32])=[CH:26][N:25]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 129227144-(Bromomethyl)-1-fluoro-2-phenoxybenzeneHCID 14718723(RS)-2-(2-methylpyrimidin-5-yl)-3,3-dimethylbutanoic acid

Product 1

HCID 147188194-fluoro-3-phenoxybenzyl (RS)-2-(2-methylpyrimidin-5-yl)-3,3-dimethylbutanoateYield 56.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Solid potassium carbonate (0.4 g) was added to a solution of 4-fluoro-3-phenoxybenzyl bromide (0.4 g) and (RS)-2-(2-methylpyrimidin-5-yl)-3,3-dimethylbutanoic acid (0.3 g) in acetone (20 cm3), and the mixture was stirred for a period of 6 hours. After standing for a further 2 days, the reaction mixture was filtered, the residue washed with acetone, and the combined filtrate and acetone washings concentrated by evaporation of the solvent under reduced pressure to give an orange oil. Column chromatography on silica gel using dichloromethane followed by ethyl acetate as eluent gave 4-fluoro-3-phenoxybenzyl (RS)-2-(2-methylpyrimidin-5-yl)-3,3-dimethylbutanoate (0.33 g) as an orange oil, which solidified on standing.

Workup

  1. waitAfter standing for a further 2 days
  2. filtrationthe reaction mixture was filtered
  3. washthe residue washed with acetone
  4. concentrationthe combined filtrate and acetone washings concentrated by evaporation of the solvent under reduced pressure
  5. customto give an orange oil

Sources & evidence

ORD record
ord-9c09588639b8415ba540900dbe06c818
Source dataset
uspto-grants-1990_10
Patent number
US04962109

Reaction notes

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