Potassium Carbonate → HCID 59363825, compound

HRID 1430631Notes

Reaction equation

HRID 1430631 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].[CH3:16][O:17][C:18](=[O:24])[CH:19](Br)[CH2:20][CH2:21][Br:22]>CN(C=O)C>[CH3:16][O:17][C:18](=[O:24])[CH:19]([O:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])[CH2:20][CH2:21][Br:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230512,4-DifluorophenolHCID 296716Methyl 2,4-dibromobutanoate

Product 1

HCID 59363825HCID 59363825, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2,4-difluoro phenol (0.35 g, 2.73 mmol) in DMF (5 ml), added potassium carbonate (0.38 g, 2.73 mmol) and 2,4-Dibromo-butyric acid methyl ester (0.71 g, 2.74 mmol) and heated at 60° C. for 3 h. Reaction mixture was cooled to r.t. It was then extracted in EtOAc (30 ml) and washed with brine (2×10 ml), dried over Na2SO4 and concentrated under reduced pressure to obtain crude product, purification on silica gel to yield 4-Bromo-2-(2,4-difluoro-phenoxy)-butyric acid methyl ester (0.52 g, 61%). 1H NMR (400 MHz, CDCl3): δ 12.42-2.56 (m, 2H), 3.53-3.71 (m, 2H), 3.77 (s, 3H), 4.81 (dd, J=3.6 and 8.8 Hz, 1H), 6.72-6.80 (m, 1H), 6.85-6.90 (m, 1H), 6.95-7.02 (m, 1H).

Workup

  1. customReaction mixture
  2. temperaturewas cooled to r.t
  3. extractionIt was then extracted in EtOAc (30 ml)
  4. washwashed with brine (2×10 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto obtain
  8. customcrude product, purification on silica gel

Sources & evidence

ORD record
ord-ca691086d15c42748d9ed09fdc8cfed2
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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