Ethyl bromoacetate → Ethyl 2-(3-fluorophenoxy)acetate

HRID 1432885Notes

Reaction equation

HRID 1432885 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O.O>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[CH3:17]

Participants

8

Reactant 4

HCID 7748Ethyl bromoacetateHCID 97433-FluorophenolHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 15078057Ethyl 2-(3-fluorophenoxy)acetateYield 93.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-fluorophenol (1.2 g, 11.8 mmol) in 20 mL of DMF at 0° C. is added sodium hydride (0.47 g, 10.7 mmol). After stirring for 10 minutes Ethyl bromoacetate (1.2 g, 10.7 mmol) is added dropwise. The reaction is allowed to warm to ambient temperatures and is stirred for 16 hours. To the reaction is added a saturated solution NH4Cl (aq.). The resulting mixture is diluted with EtOAc and H2O. The layers are separted. The organic layer is washed with H2O and a saturated solution NaCl (aq.). The organic layer is dried over MgSO4, filtered and concentrated to give the product (2 g, 10 mmol) as an oil. 1H NMR (CDCl3, 300 MHz) δ7.22 (m, 1H), 6.65 (m, 3H), 4.61 (s, 2H), 4.27 (q, 2H), 1.24 (t, 3H).

Workup

  1. additionis added dropwise
  2. temperatureto warm to ambient temperatures
  3. washThe organic layer is washed with H2O
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dd4207a3c48c469b8e912476b958cafe
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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