2-Bromoethanol → Ethanol, 2-(2,4-difluorophenoxy)-

HRID 456423Notes

Reaction equation

HRID 456423 reaction equation
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[OH:15].Br[CH2:17][CH2:18][OH:19]>CN(C=O)C.CCOC(C)=O>[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[O:15][CH2:17][CH2:18][OH:19]

Participants

6

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 1230512,4-Difluorophenol

Product 1

HCID 18437003Ethanol, 2-(2,4-difluorophenoxy)-Yield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

K2CO3 (1.07 g, 7.78 mmol) was added to a solution of 2,4-difluoro phenol (0.84 g, 6.48 mmol) in dry DMF (15 ml). 2-Bromoethanol (0.81 g, 6.48 mmol) was added, and the mixture was heated overnight at 120° C. The mixture was cooled, taken up in EtOAc, extracted with water (20 ml), saturated NaCl (4×20 ml), dried over MgSO4, and evaporated under reduced pressure. The product was purified by column chromatography on silica (Hexane:EtOAc 3:1) to give the desired product in 63% yield

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with water (20 ml), saturated NaCl (4×20 ml)
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure
  5. customThe product was purified by column chromatography on silica (Hexane:EtOAc 3:1)

Sources & evidence

ORD record
ord-7822b5b024794f6caa5ba6b2612575dc
Source dataset
uspto-grants-2007_03
Patent number
US07186726B2

Reaction notes

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