Water → HCID 28945830, compound

HRID 1888750Notes

Reaction equation

HRID 1888750 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[OH:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH:19]1[CH2:21][CH2:20]1.O>C(O)C>[CH:19]1([CH2:18][O:10][C:3]2[CH:4]=[CH:5][C:6]([CH2:8][OH:9])=[CH:7][C:2]=2[F:1])[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 112405443-Fluoro-4-hydroxybenzenemethanol

Product 1

HCID 28945830HCID 28945830, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 2-fluoro-4-(hydroxymethyl)phenol (1.08 g, 7.61 mmol) and potassium carbonate (2.10 g, 15.2 mmol) in ethanol (15 mL) was added bromomethylcyclopropane (1.54 g, 11.4 mmol), and the mixture was stirred at 70° C. for 4 hr. Water was added thereto, and the mixture was extracted twice with ethyl acetate, and the extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to hexane:ethyl acetate=3:2) to give the title compound (777 mg, yield 52%) as a white solid.

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washthe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-8a29cb71ecc64002b857175a05cc0c2c
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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