4-Fluorophenol → (2-(4-Fluorophenoxy)-ethyl)-carbamic acid tert-butyl ester

HRID 12400

Reaction equation

HRID 12400 reaction equation
Br[CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[F:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Product 1

HCID 23134036(2-(4-Fluorophenoxy)-ethyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To the crude product (700 mg) of t-butyl 2-bromoethylcarbamate obtained in Step 1 were added 4-fluorophenol (875 mg), potassium carbonate (1.08 g) and DMF (7 ml), and the mixture was stirred overnight at 90° C. The solvent was evaporated, and the mixture was diluted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated. The obtained crude product was purified by silica gel chromatography (ethyl acetate-hexane) to give t-butyl 2-(4-fluorophenoxy)ethylcarbamate (390 mg).

Workup

  1. customThe solvent was evaporated
  2. additionthe mixture was diluted with ethyl acetate
  3. washAfter washing with water
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe obtained crude product
  7. customwas purified by silica gel chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-1f2d8b6dfd7647258a6c9672414d151f
Source dataset
uspto-grants-2010_06
Patent number
US07728005B2

Linked notes

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