Potassium Carbonate → HCID 59243107, compound

HRID 1644617Notes

Reaction equation

HRID 1644617 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([OH:16])[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10].Br[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:26]([O:25][C:23](=[O:24])[CH2:22][O:16][C:14]1[CH:13]=[C:8]([CH:7]=[C:6]([O:5][CH2:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=2[F:1])[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 58948855HCID 58948855, compound

Product 1

HCID 59243107HCID 59243107, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-(2-fluorobenzyloxy)-5-hydroxybenzoate (1.9 g, 1.0 eq., 6.9 mmole) was reacted with tert-butyl bromoacetate (1.6 g, 1.2 eq., 8.3 mmole) in the presence of potassium carbonate (2.4 g., 2.5 eq., 17.3 mmole) in dimethylformamide (5 mL) over 18 h. The product was partitioned between ethyl acetate and aqueous media. The combined organic extracts were dried over magnesium sulfate, filtered and evaporated to give 2.4 g (89% yield) of a yellow oil. The LC/MS was as expected with an (M+H+) of 391 calculated and found.

Workup

  1. customThe product was partitioned between ethyl acetate and aqueous media
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-ebf81f8ac25b4f2b8da97f1b68fe6579
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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