Potassium Carbonate → Ethyl 2-(3-(2,6-difluorobenzyloxy)phenyl)acetate

HRID 73449

Reaction equation

HRID 73449 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[F:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:22]=1[CH2:23]Br>CN(C=O)C.C(OCC)(=O)C>[F:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:22]=1[CH2:23][O:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 572437Ethyl (3-Hydroxyphenyl)acetateHCID 5814352-(Bromomethyl)-1,3-difluorobenzene

Product 1

HCID 66875326Ethyl 2-(3-(2,6-difluorobenzyloxy)phenyl)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of Ethyl 2-(3-hydroxyphenyl)acetate (4 g, 22.2 mmol) in DMF (20 ml) was added potassium carbonate (4 g, 28.9 mmol) at room temperature followed by drop wise addition of 2,6-Difluorobenzyl bromide (5.06 g, 24.4 mmol). The reaction mixture was stirred for 12 hours and taken in ethyl acetate, washed with water (2×), brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (hex:ethyl acetate 4:1) to give the title compound.

Workup

  1. washwashed with water (2×), brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography on a silica gel column (hex:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-2ee651f412704a40bed080bb95e0af14
Source dataset
uspto-grants-2014_09
Patent number
US08829058B2

Linked notes

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