2-Fluorophenol → HCID 66875158, compound

HRID 1799617Notes

Reaction equation

HRID 1799617 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25]>CN(C)C=O>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17]

Participants

5

Reactant 3

HCID 97072-FluorophenolHCID 11430Potassium CarbonateHCID 1087001-Nonanol, 9-bromo-

Product 1

HCID 66875158HCID 66875158, compoundYield 107.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (2.59 g, 18.7 mmol) and 9-bromo-1-nonanol (1.39 g, 6.24 mmol) were added at room temperature to a solution of 2-fluorophenol (700 mg, 6.24 mmol) in N,N-dimethylformamide (20 mL), then after 40 h insoluble material was removed by filtration. The filtrate was evaporated and the residue taken up in dichloromethane, washed with 1 M aq. sodium hydroxide solution, dried over sodium sulfate, filtered, and evaporated, to afford 9-(2-fluoro-phenoxy)-nonan-1-ol (1.7 g), which was directly used in the next step.

Workup

  1. customafter 40 h insoluble material was removed by filtration
  2. customThe filtrate was evaporated
  3. washwashed with 1 M aq. sodium hydroxide solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-8397241a9fad467dbcf05df0579dc679
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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